89694-46-2|2-Chloro-5-methoxyphenylboronic Acid| Ambeed

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Product Details of [ 89694-46-2 ]

CAS No. :	89694-46-2	MDL No. :	MFCD06659858
Formula :	C₇H₈BClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	REFXAANPQCJZRY-UHFFFAOYSA-N
M.W :	186.40	Pubchem ID :	17750233
Synonyms :

Calculated chemistry of [ 89694-46-2 ] Expand+

Safety of [ 89694-46-2 ]

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

Application In Synthesis of [ 89694-46-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 89694-46-2 ]

[ 89694-46-2 ] Synthesis Path-Downstream 1~21

1
m-Methoxy-benzolboronsaeureanhydrid [ No CAS ]
[ 89694-46-2 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 825 - 829

2
[ 89694-46-2 ]
2-Chlor-5-methoxy-benzolboronsaeure-anhydrid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 825 - 829

4
[ 867330-26-5 ]
[ 89694-46-2 ]
[ 867330-72-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 4h;Heating / reflux;	Example 50 Synthesis of 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (33.47 mmol, 1.0 equiv), 1-chloro-4-methoxy-2-boronic acid (50.21 mmol, 1.5 equiv), Pd(PPH3)4 (3.347 mmol, 0.1 equiv), and Na2CO3 (133.9 mmol, 4.0 equiv) dissolved in DME/EtOH/water 6:1:1 and refluxed at 100° C. under an argon blanket for 4 h. The reaction was cooled to room temperature and diluted with 100 mL DCM and filtered. Precipitate recovered was suspended in water, filtered and rinsed with ether. Precipitate afforded product: 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine, a green solid (8.37 g, 84percent yield). Rf=0.85 (9:1 DCM/MeOH). 1H NMR (DMSO-d6): delta 3.35 (s, 6H), 7.01 (dd, J=8.8 Hz, J=3.0, 1H), 7.09 (d, J=3.0 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.75 (bm, 2H). MS (ES+) m/z=303. LC retention time 3.03 min.

Reference： [1]Patent: US2005/245524,2005,A1 .Location in patent: Page/Page column 38; 40
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 1546 - 1559
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 602 - 608

5
[ 745020-22-8 ]
[ 89694-46-2 ]
[ 298-12-4 ]
[ 918810-91-0 ]

Yield	Reaction Conditions	Operation in experiment
25%	In N,N-dimethyl-formamide; acetonitrile; at 85℃; for 0.5h;	A mixture of 2-chloro-5-methoxyhenylboronic acid (43 mg, 0.23 mmol), Intermediate 1 (72 mg, 0.2 mmol) and glyoxylic acid monohydrate (21 mg, 0.23 mmol) in acetonitrile (0.7 mL) and DMF (0.07 mL) was heated at 85° C. for 30 min in a Microwave Reactor. The crude product was purified by flash column chromatography (CH2Cl2:MeOH=100:15) to give 28 mg (25percent) of 77A as a solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 1.16 (s, 18 H) 3.24 (s, 3 H) 5.55 (s, 1 H) 6.57 (d, J=2.20 Hz, 1 H) 6.75-6.84 (m, 2 H) 7.00 (d, J=3.08 Hz, 1 H) 7.10-7.20 (m, 1 H) 7.27 (d, J=9.23 Hz, 1 H) 7.32 (d, J=5.27 Hz, 1 H) 7.54 (d, J=9.23 Hz, 1 H) 7.93 (d, J=6.15 Hz, 1 H); LC MS 558 (M+H).

Reference： [1]Patent: US2007/3539,2007,A1 .Location in patent: Page/Page column 76

6
[ 89694-46-2 ]
[ 1458-01-1 ]
[ 936249-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 70 - 75℃; for 2h;	Method D To a suspension of <strong>[1458-01-1]3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester</strong> (10.9 g, 53.7 mmol) in 220 ml 1,4-dioxane and water (40 ml) was added 2-chloro-5-methoxybenzene boronic acid (20 g, 107 mmol), cesium carbonate (17.5 g, 53.7 mmol) and palladium tetrakis(triphenylphosphine) (620 mg, 0.54 mmol). The reaction was heated in an oil bath at 70-75° C. for 2 hours. The reaction was then cooled and poured into 500 ml water. The resulting slurry was stirred for 10 minutes before filtering under vacuum. The beige solid collected was then slurried in 100 ml methanol, stirred for 15 minutes, then filtered, washing the filter cake with methanol and vacuum drying to afford 17.4 g of the title product. 1H-NMR (d6-DMSO): NMR (DMSO): 3.65 (s, 3H), 3.75 (s, 3H), 6.4 (br s 2H), 6.9 (d, 1H), 7.0 (dd, 1H), 7.05 (br, s, 2H), 7.4 (d, 2H). LCMS Rt=3.74 min MS m/z 309 [MH]+

Reference： [1]Patent: US2007/105872,2007,A1 .Location in patent: Page/Page column 27

7
[ 856851-34-8 ]
[ 89694-46-2 ]
[ 1079401-92-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In ethanol; water; toluene; at 20℃;Heating / reflux;Product distribution / selectivity;	To 3-iodopyridine-2,6-diamine (Preparation 44, 3.0 g, 12.8 mmol), 5-methoxy-2- chlorophenylboronic acid (2.62 g, 14.0 mmol), sodium carbonate (1.49 g, 14.0 mmol), ethanol (15 ml), water (15 ml) and tris(dibenzylideneacetone)dipalladium (0) (175 mg,0.19 mmol) at ambient temperature under a nitrogen atmosphere was added tri- <n="142"/>terfbutylphosphine (1M in toluene, 0.574 ml, 0.574 mmol). The brown mixture was heated to reflux and maintained until reaction completion by HPLC. The reaction was cooled to ambient and the ethanol removed by vacuum distillation. 2- methyltetrahydrofuran (30 ml) was then added and the biphasic mixture filtered over arbocel.(TM)., extracted with saturated aqueous sodiumhydrogencarbonate (20 ml) and separated. The organic layer was extracted five times with 10percent w/v citric acid (20 ml), then to the combined aqueous layers was added 2-methyltetrahydrofuran (30 ml) then 5M sodium hydroxide until obtaining a pH>10. The layers were separated and the upper organic layer was concentrated to dryness in vacuo obtaining product as a beige solid 2.90 g (91percent yield).
55%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 19h;Product distribution / selectivity;	To a suspension of 3-iodopyridine-2,6-diamine (Preparation 44, 2 g, 8.51 mmol) in 1 ,4- dioxane (10 ml) and water (5 ml) was added <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (0.793 g, 4.25 mmol), cesium carbonate (2.77 g, 8.51 mmol) and palladium tetrakis(triphenylphosphine) (0.123 g, 0.0125 mmol). The reaction was purged with nitrogen and heated at 80QC for 20 minutes. Three further portions of palladium tetrakis(triphenylphosphine) (0.123 g, 0.0125 mmol) and <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (0.793 g, 4.25 mmol) were added at 20 minute intervals. The reaction was heated at 8O0C for 18 hours before concentrating in vacuo. The residue was taken up in ethyl acetate (20 ml) and washed with a saturated aqueous solution of brine (20 ml) before drying over Na2SO4 and concentrating in vacuo. The residue was purified by silica gel column chromatography, eluting with 50:50 to 100:0 ethyl acetate-.pentane to afford the title compound as a brown foam (1.157 g, 55percent yield). MS m/z 250 [MH]+1HNMR (CDCI3): 3.79 (s, 3H), 4.23 (br s, 2H), 4.32 (br s, 2H), 6.00 (d, 1 H), 6.86 (m,2H), 7.14 (d, 1 H), 7.38 (d, 1 H)

Reference： [1]Patent: WO2008/135826,2008,A2 .Location in patent: Page/Page column 139; 140
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 650 - 654
[3]Patent: WO2008/135826,2008,A2 .Location in patent: Page/Page column 139

8
[ 942438-82-6 ]
[ 89694-46-2 ]
4-Amino-8-(2-chloro-5-methoxyphenyl)-7-fluoro-cinnoline-3-carboxylic acid propylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		EXAMPLE 92 4-Amino-8-(2-chloro-5-methoxyphenyl)-7-fluoro-cinnoline-3-carboxylic acid propylamide The title compound was prepared from 4-amino-7-fluoro-8-iodo-N-propylcinnoline-3-carboxamide (250 mg, 0.67 mmol) and <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (279 mg, 1.50 mmol) according to Method A to afford a solid (181 mg, 72percent). 1H NMR (500.333 MHz, CDCl3) delta 8.41 (s, 1H), 7.90 (dd, J=9.1, 5.1 Hz, 1H), 7.49 (t, J=8.7 Hz, 1H), 7.41 (dd, J=6.9, 2.7 Hz, 1H), 6.94-6.92 (m, 2H), 3.79 (s, 3H), 3.44 (q, J=6.7 Hz, 2H), 1.65 (sextet, J=7.2 Hz, 2H), 0.99 (t, J=7.3 Hz, 3H). MS APCI, m/z=389/391 (M+H). HPLC 2.13 min.

Reference： [1]Patent: US2008/318925,2008,A1

9
[ 89694-46-2 ]
[ 431942-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; In acetonitrile; at 20℃;	Method 12B; Method 12A was used except NCS was substituted for NBS.

Reference： [1]Patent: US2009/215777,2009,A1 .Location in patent: Page/Page column 45; 60
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 5942 - 5955

10
[ 89694-46-2 ]
[ 190273-89-3 ]
[ 1234096-83-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	Synthesis of intermediate 2 6-(2-Chloro-5-methoxy~phenyi)-quinazolin-2- ylamine; To a solution of 2-chloro-5-methoxy boronic acid (14.42g, 77.34 mmol, 1.5eq), 6-Bromo-quinazolin~2~ylamine ( 11.55g, 51.56 mmol, leq) and Na2CO3 (21.86g, 206.23 mmol, 4eq) in a mixture of 120ml DMF/3ml EtOH/30m. H2O, was added 2.311g (5.16 mmol, 0.1 eq) of tetrakis(tpiphenylphospine) palladium. The reaction was refluxed(1000C) for 2 hours under argon. It was then cooled off to room temperature to extract the product by DCM and brine. The product is then washed with water and ether, then dried to give 9.010 g (32 mmol, 61percent) of a pale yellow powder.

Reference： [1]Patent: WO2010/76238,2010,A1 .Location in patent: Page/Page column 21

11
[ 89694-46-2 ]
[ 7148-34-7 ]
[ 1112986-04-5 ]

Yield	Reaction Conditions	Operation in experiment
		A stream of nitrogen gas was bubbled through a mixture of 4,8- dichloroquinazoline (1.75 g, 8.8 mmol), <strong>[89694-46-2]2-chloro-5-methoxyphenylboronic acid</strong> (1.97 g, 10.6 mmol), 2M aqueous Na2CO3 (11 mL, 22 mmol) in dimethoxyethane (15 mL) and water (4 mL) for 10 min. Tetrakis-triphenylphosphine palladium (521 mg, 0.44 mmol) was added and the mixture was stirred at 75 0C for 6 h. The suspension was cooled and partitioned between EtOAc (60 mL) and water (30 mL). The layers were separated and the organic layer was further washed with aqueous NaHCO3 (10 mL), water (10 mL), and brine (20 mL). The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0:100 to 20:80 E:H to afford white foamy solid. MS (ESI) m/z 305.0; HRMS: calcd for CI5HI0CI2N2O + H+, 305.02429; found (ESI, [M+H]+ Obs'd), 305.0247.

Reference： [1]Patent: WO2010/59627,2010,A1 .Location in patent: Page/Page column 51

12
[ 947248-68-2 ]
[ 89694-46-2 ]
[ 1239954-94-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; for 2h;Reflux; Inert atmosphere;	To a solution of 2-Ch.oro-5-methoxy-phenylboronic acid (3.38g, 22.5 mmol, 1.5eq), 6- Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (3.2g, 15 mmol, leq) and Na2CO3 (6.36g, 60 mmol, 4eq) in a mixture of 40ml DMF/10ml EtOH/lOml H2O, was added 1.733g (1.5 mmol, 0.1 eq) of tetrakis(triphenylphospine) palladium. The reaction was refluxed for 2 hours under argon. It was then cooled off to room temperature and the product was precipitated by water, filtered, rinsed with water, ether and pentane to give a pale yellow powder (3.21 g, 13 mmol, 90percent yield).
90%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; for 2h;Reflux; Inert atmosphere;	Method 1 :Synthesis of intermediate 1 : 6-(2-Chloro-5-methoxy-phenyl)-[1 ,2,4]triazolo[1 ,5- a]pyridin-2-ylamineTo a solution of 2-Chloro-5-methoxy-phenylboronic acid (3.38g, 22.5 mmol, 1 .5eq), 6- Bromo-[1 ,2,4]triazolo[1 ,5-a]pyridin-2-ylamine (3.2g, 15 mmol, 1 eq) and Na2C03 (6.36g, 60 mmol, 4eq) in a mixture of 40ml DMF/10ml EtOH/10ml H20, was added 1 .733g (1 .5 mmol, 0.1 eq) of tetrakis(triphenylphospine) palladium. The reaction was refluxed for 2 hours under argon. It was then cooled off to room temperature and the product was precipitated by water, filtered, rinsed with water, ether and pentane to give a pale yellow powder (3.21 g, 13 mmol, 90percent yield).

Reference： [1]Patent: WO2010/92041,2010,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2011/161159,2011,A1 .Location in patent: Page/Page column 26

13
[ 56-05-3 ]
[ 89694-46-2 ]
[ 915070-17-6 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 5942 - 5955

14
[ 1112985-72-4 ]
[ 89694-46-2 ]
[ 1112985-71-3 ]
[ 1112985-74-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 2h;	Step 4: 4-(2-chloro-5-methoxyphenyl)-2-methyl-8-(trifluoromethyl)quinazoline A mixture of 2-methyl-8-(trifluoromethyl)quinazolin-4-yl trifluoromethanesulfonate (2.7 g, 7.5 mmol), <strong>[89694-46-2]2-chloro-5-methoxyphenylboronic acid</strong> (1.6 g, 9.4 mmol), K3PO4 (4.0 g, 18.8 mmol) and Pd(PPh3)4 (433 mg, 0.4 mmol) in dioxane (25 mL) was heated at 100° C. for 2 h. The mixture was poured into a mixture of EtOAc (100 mL) and water (70 mL) and the layers were separated. The organic layer was washed with NaHCO3 (2*50 mL), water (50 mL), and brine (70 mL). The solution was concentrated and the residue was redissolved in ~15 mL of DCM. The solution was filtered (900 mg of 2-methyl-8-(trifluoromethyl)quinazolin-4(3H)-one was recovered) and the supernatent was added to a column of SiO2 which was eluted with a gradient of 0:100 to 20:80 EtOAc:Hex. The product was isolated as a white foam. MS (ES) m/z 352.9; HRMS: calcd for C17H12ClF3N2O+H+, 353.06630; found (ESI, [M+H]+ Obs'd), 353.0668.

Reference： [1]Patent: US2010/273816,2010,A1 .Location in patent: Page/Page column 36

15
[ 608-30-0 ]
[ 89694-46-2 ]
[ 1257236-13-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 150℃; for 1h;Microwave irradiation;	<strong>[89694-46-2]2-chloro-5-methoxyphenylboronic acid</strong> (1.25 g, 6.71 mmol), 2,6-dibromoaniline (1.851 g, 7.38 mmol), sodium carbonate (6.71 mL, 13.41 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.465 g, 0.40 mmol) were dissolved in dioxane (10 mL), degassed and sealed into a microwave tube. The reaction was heated to 1500C for 1 hour in the microwave reactor and cooled to room temperature.The reaction mixture was poured into saturated aqueous NH4CI solution (100 mL), extracted with EtOAc (100 mL), and the organic layer was washed with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford an orange oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 10percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 3-bromo-2'- chloro-5'-methoxybiphenyl-2-amine (0.993 g, 47 percent) as a white solid; 1H NMR (400 MHz, CDCI3) delta 3.73 (3H, s), 3.95 (2H, s), 6.61 (1 H, t), 6.73 - 6.78 (1 H, m), 6.83 (1 H, d), 6.92 - 6.94 (1 H, m), 7.31 - 7.34 (1 H, m), 7.38 - 7.40 (1 H, m)

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6066 - 6074
[2]Patent: WO2010/136778,2010,A1 .Location in patent: Page/Page column 43

16
[ 89694-46-2 ]
[ 16499-66-4 ]
[ 1112985-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 6h;Inert atmosphere;	Example 47 4-(2-chloro-5-methoxyphenyl)-8-(trifluoromethyl)quinazoline A stream of nitrogen gas was bubbled through a mixture of 4-chloro-8-(trifluoromethyl)quinazoline (660 mg, 2.83 mmol), <strong>[89694-46-2]2-chloro-5-methoxyphenylboronic acid</strong> (723 mg, 4.26 mmol), 2M aqueous Na2CO3 (4.25 mL, 8.5 mmol) in dimethoxyethane (8 mL) for 10 min. Tetrakis-triphenylphosphine palladium (168 mg, 0.14 mmol) was added and the mixture was stirred at 80° C. for 6 h. The suspension was cooled and poured into a mixture of EtOAc (60 mL) and water (30 mL). The layers were separated and the organic layer was further washed with aqueous NaHCO3 (10 mL), water (10 mL), and brine (20 mL). The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluding with a gradient of 0:100 to 20:80 E:H to afford white foamy solid (640 mg). MS (ES) m/z 338.7; HRMS: calcd for C16H10ClF3N2O+H+, 339.05065; found (ESI, [M+H]+ Obs'd), 339.0510.

Reference： [1]Patent: US2010/273816,2010,A1 .Location in patent: Page/Page column 34

17
[ 1260215-37-9 ]
[ 89694-46-2 ]
[ 1260215-96-0 ]

Yield	Reaction Conditions	Operation in experiment
5%	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.5h;Microwave irradiation;	Example 485-(4-Ammo-2-cyclopropyl-5-methyl-2H-imidazoI-2-yI)-2'-chloro-5'-methoxybiphenyI-2-ol2-Chloro-5-methoxyphenylboronic acid (93 mg, 0.50 mmol), 4-(4-amino-2-cyclopropyl-5-methyl-2H-imidazol-2-yl)-2-bromophenol (153.5 mg, 0.50 mmol), [1,1'- bis(diphenylphosphino)ferrocene]palladium(II) chloride (20.49 mg, 0.02 mmol), cesium carbonate (487 mg, 1.49 mmol) and DMErEtOH: Water 6:3:1 (4.00 mL) were put in a microwave vial and irradiated in a microwave reactor at 150 0C for 30 min, and then concentrated in vacuo. Dichloromethane and methanol were added to the residue and the resulting mixture was filtered through a syringe filter. The filtrate was concentrated in vacuo And the residue purified by silica chromatography using 0percent to 10percent (3.5 M ammonia in methanol) in dichloromethane. The desired fractions were pooled and concentrated in vacuo and purified by preparative HPLCto give 5-(4-amino-2-cyclopropyl-5-methyl-2H-imidazol-2-yl)-2'-chloro-5'-methoxybiphenyl-2-ol (9.80 mg, 5percent yield): 1H NMR (500 MHz, DMSO-J6) delta ppm 9.36 (br. s., 1 H), 7.34 - 7.41 (m, 2 H), 7.24 (d, 1 H), 6.92 (dd, 1 H), 6.80 (dd, 2 H), 6.36 (br. s., 2 H), 3.75 (s, 3 H), 2.12 (s, 3 H), 1.37 - 1.45 (m, 1 H), 0.24 - 0.33 (m, 2 H), 0.14 - 0.22 (m, 1 H), -0.07 - 0.00 (m, 1 H); MS (ES-) m/z 368 [M-H]"; MS (ES+) m/z 370 [MH-H]+.

Reference： [1]Patent: WO2011/2408,2011,A1 .Location in patent: Page/Page column 108

18
[ 89694-46-2 ]
[ 151266-23-8 ]
3-(2-chloro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; at 80℃; for 12.5h;Inert atmosphere;	Intermediate 873-(2-chloro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1.0770 g, 4.12 mmoles) in DMF (10 ml), ethanol (5 ml) and water (5 ml), 2-chloro-5-methoxyphenyl boroinc acid (1.00 g, 5.364 mmoles) and sodium carbonate (2.186 g, 20.63 mmoles) were added and the system is degassed for 30 min. Tetrakis triphenylphosphine Palladium (0.905 g, 0.783 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as green solid (0.090 g, 16percent yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 13.61 (s, 1H), 8.19 (s, 1H), 7.51 (d, J=8.9 Hz, 1H), 7.09 (d, J=8.9 Hz 1H), 7.06 (d, J=2.6 Hz 1H), 3.78 (s, 3H).

Reference： [1]Patent: US2011/118257,2011,A1 .Location in patent: Page/Page column 97

19
[ 89694-46-2 ]
[ 1300584-91-1 ]

Reference： [1]Patent: US2011/118257,2011,A1

20
[ 89694-46-2 ]
[ 1300584-92-2 ]

Reference： [1]Patent: US2011/118257,2011,A1

21
[ 89694-46-2 ]
[ 1257236-15-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6066 - 6074
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6066 - 6074

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Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Chan-Lam Coupling Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Halogenation of Phenols • Hiyama Cross-Coupling Reaction • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reimer-Tiemann Reaction • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Vilsmeier-Haack Reaction

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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

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