[ CAS No. 89490-05-1 ]

Name: 89490-05-1|Cyclohex-1-en-1-ylboronic acid|97%
Brand: Ambeed
SKU: A275978
Rating: 95 (40 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 89490-05-1 * Storage: {[proInfo.prStorage]}

Cart0 Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 88K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 89490-05-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89490-05-1 ]

SDS

Alternatived Products of [ 89490-05-1 ]

Product Details of [ 89490-05-1 ]

CAS No. :	89490-05-1	MDL No. :	MFCD02179497
Formula :	C₆H₁₁BO₂	Boiling Point :	261.9°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	125.96 g/mol	Pubchem ID :	3862902
Synonyms :

Safety of [ 89490-05-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89490-05-1 ]

Upstream synthesis route of [ 89490-05-1 ]
Downstream synthetic route of [ 89490-05-1 ]

[ 89490-05-1 ] Synthesis Path-Upstream 1~5

1
[ 2044-08-8 ]
[ 1195-66-0 ]
[ 89490-05-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iodine; magnesium In tetrahydrofuran at 40 - 55℃; Inert atmosphere	Under the protection of nitrogen, adding magnesium metal in the reaction bottle 8.0g (0.33mol) and several grain of iodines, prior to dropping funnel in the uniformly mixed methoxy boronic acid frequency that alcohol ester 56.9g (0.36mol), cyclohexene-1-polybromide 48.3g (0.3mol) and anhydrous tetrahydrofuran 300 ml, the temperature rising to outside bath 40-45 degrees, to a first 25 ml mixed solution, after color treats the iodine triggered evanishment standard, the oven-keeping 40-55 degrees between the completion of the dropping of the remaining mixed solution, then subsequently gradually heated up to reflow to continue reaction 2-3 hours, disappearance of the raw material after detection GC, to the reaction liquid 0-10 degree, slowly adding saturated NH₄Cl quenching, adjusting for PH 5-6, separating the organic layer, the water layer using MTBE 150 ml extraction a, combined with the organic layer, the saturated salt water washing, solvent evaporation to dryness of the organic layer is concentrated under reduced pressure, then replace the high vacuum pump, collecting 80-83 °C fraction, get colorless transparent liquid 50.5g, yield 81percent

Reference： [1] Patent: CN104788481, 2016, B, . Location in patent: Paragraph 0024

2
[ 212127-64-5 ]
[ 89490-05-1 ]

Reference： [1] Journal of the American Chemical Society, 1998, vol. 120, # 31, p. 7995 - 7996

3
[ 141091-37-4 ]
[ 89490-05-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 31, p. 7799 - 7803

4
[ 18448-47-0 ]
[ 89490-05-1 ]

Reference： [1] Patent: CN104788481, 2016, B,

5
[ 89490-05-1 ]
[ 1230487-00-9 ]

Reference： [1] Patent: WO2013/113915, 2013, A1,
[2] Patent: WO2013/113915, 2013, A1,
[3] Patent: WO2017/120124, 2017, A1,

[ 89490-05-1 ] Synthesis Path-Downstream 1~24

1
[ 53848-17-2 ]
[ 89490-05-1 ]
[ 418760-99-3 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1779 - 1782

2
[ 954124-99-3 ]
[ 89490-05-1 ]
[ 954125-01-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 60℃; for 9h;	To a mixture of 2-(3-bromo-4-nitro-phenyl)-malonic acid dimethyl ester (as prepared in the previous step, 300 mg, 0.903 mmol), cyclohex-1-enyl boronic acid (125 mg, 0.994 mmol) and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (Pd(dppf)Cl2) (66.0 mg, 0.0903 mmol) in 5 mL of DMF was added K3PO4 (765 mg, 3.61 mmol). The resulting mixture was stirred at 60° C. for 9 h under Ar. After cooling to RT, the mixture was treated with 50 mL of EtOAc, washed with H2O (3.x.10 mL) and brine (10 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with 10percent EtOAc-hexane to afford 210 mg (70percent) of the title compound as a yellow oil: Mass spectrum (ESI, m/z): Calcd. for C17H19NO6, 334.1 (M+H), found 334.0.
70%	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 60℃; for 9h;	b) 2-(3-Cyclohex-1-enyl-4-nitro-phenyl)-malonic acid dimethyl ester To a mixture of 2-(3-bromo-4-nitro-phenyl)-malonic acid dimethyl ester (as prepared in the previous step, 300 mg, 0.903 mmol), cyclohexane-1-enyl boronic acid (125 mg, 0.994 mmol) and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (Pd(dppf)Cl2-CH2Cl2) (66.0 mg, 0.0903 mmol) in 5 mL of DMF was added K3PO4 (765 mg, 3.61 mmol). The resulting mixture was stirred at 60° C. for 9 h under Ar. After cooling to RT, the mixture was treated with 50 mL of EtOAc, washed with H2O (3*10 mL) and brine (10 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with 10percent EtOAc-hexane to afford 210 mg (70percent) of the title compound as a yellow oil: Mass spectrum (ESI, m/z): Calcd. for C17H19NO6, 334.1 (M+H), found 334.0.

Reference： [1]Patent: US2007/249649,2007,A1 .Location in patent: Page/Page column 42
[2]Patent: US2007/249593,2007,A1 .Location in patent: Page/Page column 41

3
[ 954424-43-2 ]
[ 89490-05-1 ]
[ 954424-44-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 2.5h;	A solution of 133 mg (0.381 mmol) of 2-bromo-4-[2-(morpholine-4-sulfonyl)-ethyl]-phenylamine (as prepared in the previous step) in toluene (6 mL) and EtOH (3 mL) was treated with 1.52 mL (3.05 mmol) of 2.0 M aqueous Na2CO3 and 60.0 mg (0.476 mmol) of <strong>[89490-05-1]cyclohex-1-enylboronic acid</strong>. The mixture was degassed via sonication, placed under Ar, treated with 30.8 mg (0.027 mmol) of Pd(PPh3)4, and heated to 80° C. for 2.5 h. The mixture was cooled to RT, diluted with EtOAc (20 mL), and washed with saturated aqueous NaHCO3 (1.x.15 mL) and brine (1.x.15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 132 mg (99percent) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C18H26N2O3S, 351.2 (M+H), found 351.1.

Reference： [1]Patent: US2007/249649,2007,A1 .Location in patent: Page/Page column 52
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6363 - 6369

4
[ 954424-50-1 ]
[ 89490-05-1 ]
2-(4-amino-3-cyclohex-1-enyl-phenyl)-ethanesulfonic acid dimethylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 17.5h;	A solution of 477 mg (1.55 mmol) of 2-(4-amino-3-bromo-phenyl)-ethanesulfonic acid dimethylamide (as prepared in the previous step) in toluene (13 mL) and EtOH (6.5 mL) was treated with 215 mg (1.71 mg) of <strong>[89490-05-1]cyclohex-1-enylboronic acid</strong> and 6.21 mL (12.4 mmol) of 2.0 M aqueous Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 179 mg (0.155 mmol) of Pd(PPh3)4, and heated to 80° C. for 17.5 h. The mixture was cooled to RT, diluted with EtOAc (50 mL), and washed with water (2.x.25 mL). The aqueous layer was extracted with EtOAc (30 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50percent EtOAc-hexane afforded 365 mg (76percent) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): delta 6.90 (dd, 1H, J=8.4, 2.4 Hz), 6.84 (d, 1H, J=2.4 Hz), 6.62 (d, 1H, J=8.4 Hz), 5.70-5.66 (m, 1H), 4.03 (br s, 2H), 3.20-3.13 (m, 2H), 2.93-2.87 (m, 2H), 2.83 (s, 6H), 2.24-2.17 (m, 4H), 1.82-1.74 (m, 2H), 1.74-1.66 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C16H24N2O2S, 309.2 (M+H), found 309.1.

Reference： [1]Patent: US2007/249649,2007,A1 .Location in patent: Page/Page column 54

5
[ 954424-55-6 ]
[ 89490-05-1 ]
2-(4-amino-3-cyclohex-1-enyl-phenyl)-ethanesulfonic acid methylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 19h;	A solution of 177 mg (0.604 mmol) of 2-(4-amino-3-bromo-phenyl)-ethanesulfonic acid methylamide (as prepared in the previous step) in toluene (5 mL) and EtOH (2.5 mL) was treated with 83.7 mg (0.664 mmol) of <strong>[89490-05-1]cyclohex-1-enylboronic acid</strong> and 2.40 mL (4.83 mmol) of 2.0 M aqueous Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 67.3 mg (0.0604 mmol) of Pd(PPh3)4, and heated to 80° C. for 19 h. The mixture was diluted with EtOAc (15 mL) and washed with water (1.x.10 mL). The aqueous layer was extracted with EtOAc (1.x.10 mL), and the combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 50percent EtOAc-hexane afforded 123 mg (69percent) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): delta 6.90 (dd, 1H, J=8.0, 2.0 Hz), 6.83 (d, 1H, J=2.0 Hz), 6.32 (d, 1H, J=8.0 Hz), 5.70-5.66 (m, 1H), 4.97-4.90 (m, 2H), 4.08-3.99 (br s, 2H), 3.24-3.17 (m, 2H), 2.91-2.84 (m, 2H), 2.66 (d, 3H, J=5.2 Hz), 2.24-2.15 (m, 4H), 1.82-1.74 (m, 2H), 1.74-1.66 (m, 2H).

Reference： [1]Patent: US2007/249649,2007,A1 .Location in patent: Page/Page column 57

6
[ 954124-25-5 ]
[ 89490-05-1 ]
[ 954124-27-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		k) 4-(4-Amino-3-cyclohex-1-enyl-phenyl)-piperidine-2,6-dione A solution of 69.0 mg (0.244 mmol) of 4-(4-amino-3-bromo-phenyl)-piperidine-2,6-dione (as prepared in the previous step) in toluene (10 mL) and dioxane (10 mL) was treated with 30.7 mg (0.244 mmol) of <strong>[89490-05-1]cyclohex-1-enylboronic acid</strong>, 104 mg (0.487 mmol) of K3PO4, and 34.2 mg (0.0975 mmol) of 2-(dicyclohexylphosphino)biphenyl. The mixture was degassed via sonication, placed under Ar, treated with 5.50 mg (0.0244 mmol) of Pd(OAc)2, and heated to 90° C. for 5 h. The mixture was diluted with EtOAc (30 mL) and washed with water (2*20 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 73.5 mg (106percent, some solvent trapped) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C17H20N2O2, 285.2 (M+H), found 285.2.

Reference： [1]Patent: US2007/249593,2007,A1 .Location in patent: Page/Page column 25

7
[ 954124-93-7 ]
[ 89490-05-1 ]
[ 954124-95-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		d) 4-(4-Amino-3-cyclohex-1-enyl-phenyl)-1-methyl-piperidine-2,6-dione A suspension of 265 mg (0.892 mmol) of 4-(4-amino-3-bromo-phenyl)-1-methyl-piperidine-2,6-dione (as prepared in the previous step) in toluene (15 mL) and dioxane (15 mL) was treated with 379 mg (1.78 mmol) of K3PO4, 146 mg (1.16 mmol) of <strong>[89490-05-1]cyclohex-1-enylboronic acid</strong>, and 125 mg (0.357 mmol) of 2-(dicyclohexylphosphino)-biphenyl. The mixture was degassed via sonication, placed under Ar, treated with 20.0 mg (0.00892 mmol) of Pd(OAc)2, and heated to 80° C. for 2.5 h. The mixture was diluted with EtOAc (70 mL) and washed with water (2*50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 25-50percent EtOAc-hexane afforded 266 mg (100percent) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C18H22N2O2, 299.2 (M+H), found 299.1.

Reference： [1]Patent: US2007/249593,2007,A1 .Location in patent: Page/Page column 40

8
[ 915005-98-0 ]
[ 89490-05-1 ]
[ 915005-99-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 8h;	c) 2-Cyclohex- 1 -enyl-4-( 1 -oxy-pyridin-4-yl)-phenylamine; To a mixture of 2-bromo-4-(l-oxy-pyridin-4-yl)-phenylamine (as prepared in the previous step, 240 mg, 0.905mmol), cyclohexen-1-yl boronic acid (126 mg, 0.996 mmol) and Pd(PPh3)4 (105 mg, 0.091mmol) in 9 mL of 1,4-dioxane was added 2.0 M aq Na2CO3 solution (3.62 mL, 7.24 mmol). The resulting mixture was stirred at 80 C for 8 h under Ar, and then cooled to RT. Treated with 20 mL of brine, the mixture was extracted with DCM (4 x 20 mL). The combined organic layers were concentrated in vacuo and purified by flash chromatography on silica gel (2-5 percent MeOH/DCM) to give 241 mg (100 percent) of the title compound as a light <n="53"/>yellow solid. 1H-NMR (CDCl3; 400 MHz): delta 8.18 (d, 2H, J = 7.3 Hz), 7.44 (d, 2H, J = 7.3 Hz), 7.30 (dd, IH, J = 8.4, 2.2 Hz), 6.76 (d, IH, J = 8.4 Hz), 5.80 (m, IH), 3.0-4.2 (br s, 2H), 2.17- 2.28 (m, 4H), 1.68-1.82 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C17H18N2O, 267.1 I(M+H), found 267.1.

Reference： [1]Patent: WO2007/123516,2007,A1 .Location in patent: Page/Page column 50-51
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3925 - 3929

9
[ 51605-97-1 ]
[ 89490-05-1 ]
[ 915006-03-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 8h;	Example 22; 4-Cyano-lH-imidazole-2-carboxylic acid (2-cyclohex-l-enyl-4-isopropyl-phenyl)-amide; a) 2-Cyclohex- 1 -enyl-4-isopropyl-phenylamine; <n="60"/>To a mixture of 2-bromo-4-isopropyl-phenylamine (214 mg, 1.00 mmol), cyclohexane-1- enyl boronic acid (139 mg, 1.10 mmol) and Pd(PPh3)4 (116 mg, 0.100 mmol) in 5 mL of 1,4- dioxane was added 2.0 M aqueous Na2CO3 solution (4.0 mL, 8.0 mmol). The resulting mixture was stirred at 80 C for 8 h under Ar, and then cooled to RT. The reaction was treated with EtOAc (20 mL) and washed with H2O (2 x 10 mL) and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (DCM) to give 205 mg (95 percent) of the title compound as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C15H21N, 216.2 (M+H), found 216.1.

Reference： [1]Patent: WO2007/123516,2007,A1 .Location in patent: Page/Page column 57-58

10
[ 915006-30-3 ]
[ 89490-05-1 ]
[ 915006-31-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 3.5h;	b) 2-Cyclohex-l-enyl-4-(morpholine-4-sulfonyl)-phenylamine; <n="94"/>A solution of 50.0 mg (0.156 mmol) of 2-bromo-4-(morpholine-4-sulfonyl)- phenylamine (as prepared in the previous step) in toluene (4 niL) and EtOH (2 mL) was treated with 623 muL (1.25 mmol) of 2.0 M aqueous Na2CO3 and 20.6 mg (0.163 mmol) of cyclohex-1- enylboronic acid. The mixture was degassed via sonication, placed under Ar, treated with 12.6 mg (0.0109 mmol) of Pd(PPh3)4, and heated to 80 0C for 3.5 h. The mixture was cooled to RT, stirred for 16 h, diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (I x 10 mL) and brine (1 x 10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 25- 50 percent EtOAc-hexane afforded 20.0 mg (40 percent) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C16H22N2O3S, 323.1 (M+H), found 323.1.

Reference： [1]Patent: WO2007/123516,2007,A1 .Location in patent: Page/Page column 91-92
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6363 - 6369

11
[ 885693-07-2 ]
[ 89490-05-1 ]
2-cyclohex-1-enyl-4-(1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-yl)-phenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 20℃; for 1h;	To a mixture of 2-bromo-4-(l,l-dioxo-hexahydro-llambda6-thiopyran-4-yl)-phenylamine (as prepared in the previous step, 150 mg, 0.493 mmol), cyclohexen-1-yl boronic acid (70 mg, 0.542 mmol) and Pd(PPh3J4 (57 mg, 0.0493 mmol) in 5 mL of 1,4-dioxane was added 2.0 M aq Na2CO3 solution (2.0 mL, 4.0 mmol). The resulting mixture was stirred at 80 °C for 8 h under Ar, and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H2O (3 x 15 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (2-5 percent EtOAc/DCM) gave 130 mg (86 percent) of the title compound as a brown solid. 1H-NMR EPO <DP n="81"/>(CDCl3; 400 MHz): delta 6.89 (dd, IH, J = 8.4, 2.3 Hz), 6.84 (d, IH, J = 2.3 Hz), 6.65 (d, IH, J - 8.4 Hz), 5.74 (m, IH), 3.74 (br s, 2H), 3.08-3.17 (m, 4H), 2.66 (dddd, IH, J = 12.1, 12.1, 3.1, 3.1 Hz), 2.29-2.42 (m, 2H), 2.13-2.25 (m, 6H), 1.73-1.81 (m, 2H), 1.65-1.73 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for Ci7H23NO2S, 306.1 (M+H), found 306.1.
86%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 8h;	To a mixture of 2-bromo-4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-phenylamine (as prepared in the previous step, 150 mg, 0.493 mmol), cyclohexen-1-yl boronic acid (70 mg, 0.542 mmol) and Pd(PPh3)4 (57 mg, 0.0493 mmol) in 5 mL of 1,4-dioxane was added 2.0 M aq Na2CO3 solution (2.0 mL, 4.0 mmol). The resulting mixture was stirred at 80° C. for 8 h under Ar, and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H2O (3.x.15 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (2-5percent EtOAc/DCM) gave 130 mg (86percent) of the title compound as a brown solid. 1H-NMR (CDCl3; 400 MHz): delta 6.89 (dd, 1H, J=8.4, 2.3 Hz), 6.84 (d, 1H, J=2.3 Hz), 6.65 (d, 1H, J=8.4 Hz), 5.74 (m, 1H), 3.74 (br s, 2H), 3.08-3.17 (m, 4H), 2.66 (dddd, 1H, J=12.1, 12.1, 3.1, 3.1 Hz), 2.29-2.42 (m, 2H), 2.13-2.25 (m, 6H), 1.73-1.81 (m, 2H), 1.65-1.73 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C17H23NO2S, 306.1 (M+H), found 306.1.
86%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 8h;	f) 2-Cyclohex-1-enyl-4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-phenylamine To a mixture of 2-bromo-4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-phenylamine (as prepared in the previous step, 150 mg, 0.493 mmol), cyclohexen-1-yl boronic acid (70 mg, 0.542 mmol) and Pd(PPh3)4 (57 mg, 0.0493 mmol) in 5 mL of 1,4-dioxane was added 2.0 M aq Na2CO3 solution (2.0 mL, 4.0 mmol). The resulting mixture was stirred at 80° C. for 8 h under Ar, and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H2O (3*15 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (2-5percent EtOAc/DCM) gave 130 mg (86percent) of the title compound as a brown solid. 1H-NMR (CDCl3; 400 MHz): delta 6.89 (dd, 1H, J=8.4, 2.3 Hz), 6.84 (d, 1H, J=2.3 Hz), 6.65 (d, 1H, J=8.4 Hz), 5.74 (m, 1H), 3.74 (br s, 2H), 3.08-3.17 (m, 4H), 2.66 (dddd, 1H, J=12.1, 12.1, 3.1, 3.1 Hz), 2.29-2.42 (m, 2H), 2.13-2.25 (m, 6H), 1.73-1.81 (m, 2H), 1.65-1.73 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C17H23NO2S, 306.1 (M+H). found 306.1.

86%

With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 20 - 80℃; for 8h;

To a mixture of 2-bromo-4-(l,l-dioxo-hexahydro-llambda6-thiopyran-4-yl)-phenylamine (as prepared in the previous step, 150 mg, 0.493 mmol), cyclohexen-1-yl boronic acid (70 mg, 0.542 mmol) and Pd(PPh3)4 (57 mg, 0.0493 mmol) in 5 mL of 1 ,4-dioxane was added 2.0 M aq Na2CO3 solution (2.0 mL, 4.0 mmol). The resulting mixture was stirred at 80 °C for 8 h under Ar, and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H2O (3 x 15 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (2-5 percent EtOAc/DCM) gave 130 mg (86 percent) of the title compound as a brown solid. 1H-NMR (CDCl3; 400 MHz): delta 6.89 (dd, IH, J = 8.4, 2.3 Hz), 6.84 (d, IH, J = 2.3 Hz), 6.65 (d, IH, J = 8.4 Hz)5 5.74 (m, IH), 3.74 (br s, 2H), 3.08-3.17 (m, 4H), 2.66 (dddd, IH, J = 12.1, 12.1, 3.1, 3.1 Hz), 2.29- 2.42 (m, 2H), 2.13-2.25 (m, 6H), 1.73-1.81 (m, 2H), 1.65-1.73 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C17H23NO2S, 306.1 (M+H), found 306.1.

Reference： [1]Patent: WO2006/47277,2006,A2 .Location in patent: Page/Page column 79-80
[2]Patent: US2006/281788,2006,A1 .Location in patent: Page/Page column 64-65
[3]Patent: US2008/51402,2008,A1 .Location in patent: Page/Page column 51
[4]Patent: WO2007/48088,2007,A2 .Location in patent: Page/Page column 97

12
[ 885693-49-2 ]
[ 89490-05-1 ]
5-amino-6-cyclohex-1-enyl-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 16h;	To a mixture of 5-amino-6-bromo-3l,4l,5',6'-tetrahydro-2'H-[2,4']bipyridinyl-r- carboxylic acid tert-butyl ester (331 mg, 0.93 mmol) (as prepared in Example 54, step (c)) and cyclohexen-1-yl boronic acid (141 mg, 1.11 mmol) in 5 mL of EtOH , 10 mL of toluene and 5 mL of 2 M Na2CO3, was added Pd(PPh3)4 (107 mg, 0.0930 mmol) and the result was heated at 800C for 16 h. The reaction was diluted with 100 mL of ether and 100 mL of brine and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification of the residue by column chromatography (silica gel, 30-60percent ether-hexanes) afforded 248 mg (74percent) the title compound as an light brown oil LC-MS (ESi, m/z): Calcd. for C2 , H32N3O2 (M+H), 358.2, found 358.1.
74%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 16h;	To a mixture of 5-amino-6-bromo-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester (331 mg, 0.93 mmol) (as prepared in Example 54, step (c)) and cyclohexen-1-yl boronic acid (141 mg, 1.11 mmol) in 5 mL of EtOH, 10 mL of toluene and 5 mL of 2 M Na2CO3, was added Pd(PPh3)4 (107 mg, 0.0930 mmol) and the result was heated at 80° C. for 16 h. The reaction was diluted with 100 mL of ether and 100 mL of brine and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification of the residue by column chromatography (silica gel, 30-60percent ether-hexanes) afforded 248 mg (74percent) the title compound as an light brown oil LC-MS (ESI, m/z): Calcd. for C21H32N3O2 (M+H), 358.2, found 358.1.
74%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 16h;	a) 5-Amino-6-cyclohex-1-enyl-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester To a mixture of 5-amino-6-bromo-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester (331 mg, 0.93 mmol) (as prepared in Example 54, step (c)) and cyclohexen-1-yl boronic acid (141 mg, 1.11 mmol) in 5 mL of EtOH, 10 mL of toluene and 5 mL of 2 M Na2CO3, was added Pd(PPh3)4 (107 mg, 0.0930 mmol) and the result was heated at 80° C. for 16 h. The reaction was diluted with 100 mL of ether and 100 mL of brine and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification of the residue by column chromatography (silica gel, 30-60percent ether-hexanes) afforded 248 mg (74percent) the title compound as an light brown oil LC-MS (ESI, m/z): Calcd. for C21H32N3O2 (M+H), 358.2. found 358.1.

74%

With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 16h;

To a mixture of 5-amino-6-bromo-3',4',5',6'-tctraliydro-2'H-[2,4I]bipyridinyl-l '- carboxylic acid tert-butyl ester (331 mg, 0.93 mmol) (as prepared in Example 54, step (c)) and cyclohexen-1-yl boronic acid (141 mg, 1.11 mmol) in 5 mL of EtOH , 10 mL of toluene and 5 mL of 2 M Na2CO3, was added Pd(PPh3)4 (107 mg, 0.0930 mmol) and the result was heated at 80 0C for 16 h. The reaction was diluted with 100 mL of ether and 100 mL of brine and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification of the residue by column chromatography (silica gel, 30-60percent ether-hexanes) afforded 248 mg (74percent) the title compound as an light brown oil LC-MS (ESI, m/z): Calcd. for C2IH32N3O2 (M+H), 358.2, found 358.1.

Reference： [1]Patent: WO2006/47277,2006,A2 .Location in patent: Page/Page column 127-128
[2]Patent: US2006/281788,2006,A1 .Location in patent: Page/Page column 87-88
[3]Patent: US2008/51402,2008,A1 .Location in patent: Page/Page column 73
[4]Patent: WO2007/48088,2007,A2 .Location in patent: Page/Page column 144

13
[ 1735-53-1 ]
[ 89490-05-1 ]
[ 1034188-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate;bis-triphenylphosphine-palladium(II) chloride; In methanol; at 80℃; for 0.166667h;Microwave irradiation;	Description 15; 4-(1 -cyclohexen-1-yl)-3-(trifluoromethyl)benzamide (D15); <strong>[1735-53-1]4-bromo-3-(trifluoromethyl)benzonitrile</strong> (1.2 g, 4.80 mmol), 1-cyclohexen-1-ylboronic acid (0.907 g, 7.20 mmol), sodium methoxide (0.778 g, 14.40 mmol) and bis(triphenylphosphine)palladium(ll) chloride (0.337 g, 0.480 mmol) were added to dry methanol (12 ml.) and the mixture heated in the microwave at 80 0C for 10 minutes. The reaction mixture was partitioned between ethyl acetate (40 ml.) and water (40 ml.) and then the organic phase washed with further water (40 ml_). The organic phase was dried (MgSO^, filtered and the solvent removed in vacuo. The crude product was purified by flash silica chromatography, eluting with 0-75 % ethyl acetate in hexane to give the title compound as a white solid (1.02 g). deltaH (CDCI3, 400 MHz): 8.08 (1 H, s), 7.90 (1 H, d), 7.32 (1 H, d), 6.3-5.8 (2H, m), 5.61 (1 H, s), 2.25- 2.13 (4H, m), 1.80-1.60 (4H, m) ppm. MS (ES+): Ci4H14F3NO requires 269; found 270 (M+H+).
	With methanol; sodium methylate;bis-triphenylphosphine-palladium(II) chloride; at 80℃; for 0.166667h;Microwave irradiation;	Description for D664-(1 -Cyclohexen-1 -yl)-3-(trifluoromethyl)benzamide (D66)<strong>[1735-53-1]4-bromo-3-(trifluoromethyl)benzonitrile</strong> (commercial) (1.2 g, 4.80 mmol), 1- cyclohexen-1-ylboronic acid (0.907 g, 7.20 mmol), sodium methoxide (0.778 g, 14.40 mmol) and bis(triphenylphosphine)palladium(ll) chloride (0.337 g, 0.480 mmol) were added to dry methanol (12 ml.) and the mixture heated in the microwave at 80 0C for 10 minutes. The reaction mixture was partitioned between ethyl acetate (40 ml.) and water (40 ml.) and then the organic phase washed with further water (40 ml_). The organic phase was dried (MgSC^), filtered and the solvent removed in vacuo. The crude product was purified by flash silica chromatography, eluting with 0-75 % ethyl acetate in hexane to give the title compound as a white solid (1.02 g). deltaH (CDCI3, 400 MHz): 8.09 (1 H, m), 7.90 (1 H, dd), 7.32 (1 H, d), 6.3-5.8 (2H, m) 5.61 (1 H, s), 2.25-2.13 (4H, m), 1.80-1.60 (4H, m). MS (ES): C14H14F3NO requires 269; found 270 (MH+).
	With sodium methylate;bis-triphenylphosphine-palladium(II) chloride; In methanol; at 80℃; for 0.166667h;In the microwave;	4-Bromo-3-(trifluoromethyl)benzonitrile (commercial) (1.2 g, 4.80 mmol), 1- cyclohexen-1-ylboronic acid (0.907 g, 7.20 mmol), sodium methoxide (0.778 g, 14.40 mmol) and bis(triphenylphosphine)palladium(ll) chloride (0.337 g, 0.480 mmol) were added to dry methanol (12 ml.) and the mixture heated in the microwave at 80 0C for 10 minutes. The reaction mixture was partitioned between ethyl acetate (40 ml.) and water (40 ml.) and then the organic phase washed with further water (40 ml_). The organic phase was dried (MgSC^), filtered and the solvent removed in vacuo. The crude product was purified by flash silica chromatography, eluting with 0-75 % ethyl acetate in hexane to give the title compound as a white solid (1.02 g). MS (ES): C14H14F3NO requires 269; found 270 (MH+).

Reference： [1]Patent: WO2008/74820,2008,A1 .Location in patent: Page/Page column 29
[2]Patent: WO2008/74821,2008,A1 .Location in patent: Page/Page column 72
[3]Patent: WO2008/128951,2008,A1 .Location in patent: Page/Page column 55

14
[ 161622-14-6 ]
[ 89490-05-1 ]
[ 1034188-31-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In butan-1-ol; at 100℃;	Step 5 (0262) [00248] 4-(cyclohex-1-en-1-yl)-3-(trifluoromethyl)benzoic acid: To a solution of 4- bromo-3-(trifluoromethyl)benzoic acid (7.12 g, 26.47 mmol, 1.00 equiv.) in n-BuOH (100 mL), (cyclohex-1-en-1-yl)boronic acid (3.67 g, 29.14 mmol, 1.10 equiv.), Pd(Pph3)2Cl2 (370 mg, 0.53 mmol, 0.02 equiv.), and potassium carbonate (5.48 g, 39.65 mmol, 1.50 equiv.) was added. The resulting solution was stirred overnight at 100 oC. The reaction mixture was cooled and quenched by water (200 ml). The resulting solution was extracted with ethyl acetate (3 x 100 mL) and the organic layers combined, then washed with brine (2 x 50 mL) and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column, eluted with ethyl acetate/petroleum ether (1:15). The collected fractions were combined and concentrated under vacuum to afford 6.4 g (89%) of 4-(cyclohex-1-en-1-yl)-3-(trifluoromethyl) benzoic acid as a light brown solid. LC-MS: m/z =269 [M-H]-.
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In methanol; at 95℃;Inert atmosphere;	In pressure reactor 20g <strong>[161622-14-6]4-bromo-3-(trifluoromethyl)benzoic acid</strong>, 9.37g cyclohexenylboronic acid, 0.52g bis(triphenylphosphine)palladium (II) chloride and 15.41 g potassium carbonate in 150ml methanol were carefully degassed and stirred under nitrogen at IT 95C until the reaction went to completion (3-4h). Ethylacetate (250ml) and 200ml 0.1 N HCI were added to the reaction mixture at IT = 20 - 25C. The phases were separated and the organic phase was washed with 2X 159 ml 10% NaCI in water. Then 5g charcoal were added to the organic phase, and the mixture is stirred for 30 min and filtrated. Evaporation to dryness gave 20.02g of an orange solid which contained ca 94% 4-cyclohex-1-enyl-3-trifluoromethyl-benzoic acid according to HPLC. This is used without further purification for the synthesis of 4-cyclohexyl-3- trifluoromethyl-benzoic acid 1H-NMR (400MHz, DMSO-d6): delta 1 .6-1 .8(4H,m), 2.1-2.3(41-1, m), 5.58(1 H,t), 7.48(1 H,d), 8.12- 8.17(2H,m) MS: 269.0799(M-H)"

Reference： [1]Patent: WO2017/120124,2017,A1 .Location in patent: Paragraph 00247-00248
[2]Patent: WO2013/113915,2013,A1 .Location in patent: Page/Page column 32-33

15
[ 89490-05-1 ]
[ 1230487-00-9 ]

Reference： [1]Patent: WO2013/113915,2013,A1
[2]Patent: WO2013/113915,2013,A1
[3]Patent: WO2017/120124,2017,A1

16
[ 50397-74-5 ]
[ 89490-05-1 ]
[ 915006-68-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6363 - 6369

17
[ 290368-00-2 ]
[ 89490-05-1 ]
C₁₈H₂₂N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1327 - 1333

18
[ 105752-11-2 ]
[ 89490-05-1 ]
[ 1052705-85-7 ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; In tetrahydrofuran; water; at 20℃; for 24h;	4-(Cyclohex-l-en-l-yl)pyridin-3-amine.The mixture of 4-iodopyridin-3 -amine (0.161 g, 0.734 mmol),cyclohex-l-en-l-ylboronic acid (0.0924 g, 0.734 mmol), XPhos precatalyst (0.023g, 0.029 mmol), Phosphoric acid, potassium salt (2M aq) (0.550 mL, 1.100 mmol)in THF (3.0 mL) was stirred at room temperature for 24 hours. The reaction wasdiluted with ethyl acetate and washed with water three times. The ethyl acetatelayer was separated, dried (Na2SC"4), filtered and concentrated. Flashcolumn eluted with ethyl acetate in hexane from 0 to 100% gave the desiredproduct (33 mg, 25% yield). MS(ES+) m/e 175 MS[M+H]+; 1H NMR (400MHz,CHLOROFORM-d) delta 8.06 (s, 1H), 7.95 (d, J=5.0 Hz, 1H), 6.89 - 6.85 (m, 1H), 5.86(dt, J=3.8, 1.9 Hz, 1H), 3.80 (br. s., 2H), 2.26 - 2.15 (m, 4H), 1.81 - 1.74(m, 2H), 1.73 - 1.64 (m, 2H).

Reference： [1]Patent: WO2015/69594,2015,A1 .Location in patent: Page/Page column 124

19
[ 1813-33-8 ]
[ 89490-05-1 ]
C₁₄H₁₂F₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; toluene; for 12h;Reflux;	General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6844 - 6854

20
[ 84539-34-4 ]
[ 89490-05-1 ]
3-bromo-5-(cyclohex-1-en-1-yl)pyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 130℃; for 1.5h;Inert atmosphere; Microwave irradiation;	Intermediate s:3-bromo-5-{cyclohex-1-en-1-yl)pyridln-4-amine To a stirred and nitrogen degassed solution of <strong>[84539-34-4]3,5-dibromopyridin-4-amine</strong> (CAS 84539-34-4; 2.00 g, 7.94 mmol), potassium carbonate (2.20 g, 15.88 mmol) and (cyclohex-i-en-i-yl)boronic acid (CM 89490-05-1; 1.10 g, 8.73 mmol) in dioxane (26 mL) and water (1.6 mL) was added bis(triphenylphosphine)palladium(1I) dichioride (CAS 13965-03-2; 557 mg, 794 iimol). The reaction mixture was heated under microwave irradiation at 130 C for 1.5 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organics were dried (MgSOJ, filtered and concentrated in vczczw. The crude product was purified by column chromatography (silica, 0-50% EtOAc / petroleum ether) to afford the title compound.?H NMR (400 MHz, DK{SO-d5) 6 ppm i.8 - 1.69 (m, 2 H) 1.69 - 1.78 (m, 2 H) 2.15 (br. S., 4 H) 5.62 - (m, H) 7.78 (s, i H) 8.i6 (s, iH)MS ES: 255

Reference： [1]Patent: WO2015/198045,2015,A1 .Location in patent: Page/Page column 55; 56

21
[ 6237-96-3 ]
[ 89490-05-1 ]
4-chloro-6-(cyclohex-1-en-1-yl)-2-ethylpyrimidin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100.0℃; for 0.666667h;Microwave irradiation;	Intermediate 6: 4-chloro-2-(cyclobex-1-en-I-yI)pyfldln-3-anhlne To a stirred solution of 2,4-dichloropyridin-3-amrne (CAS 173772-63-9; 750 mg, 4.60 mmol), potassium carbonate (3.18 g, 23.01 mmol) and (cyclohex-i-en-i-yl)boronie acid (CAS 89490-05-1; 869 mg, 6.go mmol) in dioxane (8 mL) and water (2 mL) was tetrakis(triphenylphosphane) palladium (532 mg, 460 iimol). The reaction mixture was heated under microwave irradiation at 140 C for 30 mm. The reaction mixture was filtered (Celite) and then poured into water and extracted with EtOAc. The combined organics were dried (H-frit) and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% EtOAc / petroleum ether) to afford the title compoundIntermediate i: 4-chIoro-6-(cyclohcx-1-en-1-yI)-2-ethylpyrirnidin-5- amine mg, 1.27 mmol) in dioxane (io mL) and water (2.5 mL). The reaction mixture was heated under microwave irradiation at 100 C for 40 mm. The crude product was purified by column chromatography (silica, 0-30% EtOAc / petroleum ether) to afford the title compound.?H NMI{ (400 MHz, DMSO-d6) 6ppm ?.17 (t, J=8 Hz, 3 H) 1.59 - 1.75 (m, 4 H) 2.14 - 2.22 (m, 2 H) 2.27- 2.34 (m, 2 H) 2.61 - 2.70 (m, 2 H) 5.14 (s, 2 H) 6.14 (br. s., I H) MS ESi 238

Reference： [1]Patent: WO2015/198045,2015,A1 .Location in patent: Page/Page column 56; 57; 62; 63

22
[ 1017781-60-0 ]
[ 89490-05-1 ]
C₁₃H₁₈N₂OS [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2018,vol. 91,p. 172 - 180

23
[ 221295-04-1 ]
[ 89490-05-1 ]
5-(cyclohex-1-en-1-yl)pyrazine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In 1,4-dioxane; water; at 95℃;Inert atmosphere;	In a dry flask under argon was added <strong>[221295-04-1]2-bromo-5-cyanopyrazine</strong> (1.84 g, 10 mmol), SPhos (410 mg, 1.0 mmol), cyclohexene-l-yl boronic acid (1.76 g, 14 mmol) and potassium phosphate tribasic (6.37 g, 30 mmol). The flask flushed with argon. Dioxane (30 mL) and water (4 mL) were added and the mixture was degassed with vacuum and backflushed with argon. Pd(OAc)2 (1 12 mg, 0.5 mmol) was added and the reaction was degassed again. The reaction mixture was stirred at 95 C for overnight. The crude reaction mixture was cooled, poured onto water and extracted with EtOAc (3X). The organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by chromatography (80: 15:5 hexane: DCM: EtOAc eluent) provided 5- (cyclohex-l-en-l-yl)pyrazine-2-carbonitrile (1.3 g, 68%). NMR (300 MHz, Chloroform- delta 8.87 - 8.70 (m, 2H), 7.10 - 6.98 (m, 1H), 2.61 - 2.49 (m, 2H), 2.43 - 2.31 (m, 2H), 1.93 - 1.79 (m, 2H), 1.78 - 1.68 (m, 2H).

Reference： [1]Patent: WO2018/136935,2018,A1 .Location in patent: Paragraph 00705; 00707

24
[ 89581-38-4 ]
[ 89490-05-1 ]
methyl 5-(cyclohex-1-en-1-yl)pyrimidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; water; at 40℃; for 14h;Inert atmosphere;	General procedure: To a solution of methyl 5-chloropyrazine-2-carboxylate (601 mg, 3.48 mmol) in THF (11.6 mL) was added 1-cyclohexene-l-yl-boronic acid (656 mg, 5.21 mmol), K3PO4 (1.47 g, 6.91 mmol), Pd(OAc)2 (39.2 mg, 0.175 mmol), SPhos (144 mg, 0.350 mmol) and H2O (0.13 mL, 7.2 mmol) at room temperature. After stirring for 15 h at 40 C, the reaction was quenched by adding water. The crude products were extracted with EtOAc (3X), and the combined organic extracts were washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc = 9/1 to 4/1) to afford methyl 5-(cyclohex-l-en-l-yl)pyrazine-2-carboxylate (736 mg, 97%) as a pale yellow solid. NMR (300 MHz, CDCh) delta 9.21 (d, J= 1.2 Hz, 1H), 8.81 (d, J= 1.2 Hz, 1H), 6.98-7.01 (m, 1H), 4.05 (s, 3H), 2.55-2.60 (m, 2H), 2.34-2.38 (m, 2H), 1.81-1.89 (m, 2H), 1.70-1.77 (m, 2H). Preparation by a similar procedure to Example 110, step 2, starting from <strong>[89581-38-4]methyl 5-bromopyrimidine-2-carboxylate</strong> to obtain methyl 5-(cyclohex-l-en-l-yl)pyrimidine-2-carboxylate. NMR (300 MHz, CDCh) delta 8.91 (s, 2H), 6.42-6.44 (m, 1H), 4.09 (s, 3H), 2.43-2.48 (m, 2H), 2.28-2.34 (m, 2H), 1.84-1.88 (m, 2H), 1.71-1.76 (m, 2H).

Reference： [1]Patent: WO2018/136935,2018,A1 .Location in patent: Paragraph 00665; 00762; 00770; 00773

Related Products

Historical Records

Related Functional Groups of
[ 89490-05-1 ]

Alkenyls

[ 850036-28-1 ]

Cyclopent-1-en-1-ylboronic acid

Similarity: 0.94

[ 141091-37-4 ]

2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.62

[ 1310384-24-7 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enol

Similarity: 0.61

[ 859217-67-7 ]

2-(4,4-Dimethyl-1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.61

[ 859217-85-9 ]

4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolane

Similarity: 0.60

Organoboron

[ 850036-28-1 ]

Cyclopent-1-en-1-ylboronic acid

Similarity: 0.94

[ 40276-63-9 ]

(2-Benzylphenyl)boronic acid

Similarity: 0.68

[ 90002-36-1 ]

2-Ethylphenylboronic acid

Similarity: 0.67

[ 103986-53-4 ]

4-Methyl-1-naphthaleneboronic acid

Similarity: 0.65

[ 1373393-41-9 ]

(2-Cyclopropylphenyl)boronic acid

Similarity: 0.65

Aliphatic Cyclic Hydrocarbons

[ 850036-28-1 ]

Cyclopent-1-en-1-ylboronic acid

Similarity: 0.94

[ 141091-37-4 ]

2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.62

[ 1310384-24-7 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enol

Similarity: 0.61

[ 859217-67-7 ]

2-(4,4-Dimethyl-1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.61

[ 859217-85-9 ]

4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolane

Similarity: 0.60

Organoboron

[ 850036-28-1 ]

Cyclopent-1-en-1-ylboronic acid

Similarity: 0.94

[ 40276-63-9 ]

(2-Benzylphenyl)boronic acid

Similarity: 0.68

[ 90002-36-1 ]

2-Ethylphenylboronic acid

Similarity: 0.67

[ 103986-53-4 ]

4-Methyl-1-naphthaleneboronic acid

Similarity: 0.65

[ 1373393-41-9 ]

(2-Cyclopropylphenyl)boronic acid

Similarity: 0.65

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 89490-05-1 ]

Quality Control of [ 89490-05-1 ]

Related Doc. of [ 89490-05-1 ]

Product Details of [ 89490-05-1 ]

Safety of [ 89490-05-1 ]

Application In Synthesis of [ 89490-05-1 ]

[ 89490-05-1 ] Synthesis Path-Upstream 1~5

[ 89490-05-1 ] Synthesis Path-Downstream 1~24

Related Functional Groups of [ 89490-05-1 ]

Alkenyls

Organoboron

Aliphatic Cyclic Hydrocarbons

Organoboron

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 89490-05-1 ]