103058-87-3|5-Bromo-2-methoxynicotinaldehyde| Ambeed

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Quality Control of [ 103058-87-3 ] Purity: 97% SDS Specification

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Product Details of [ 103058-87-3 ]

CAS No. :	103058-87-3
Formula :	C₇H₆BrNO₂
M.W :	216.03
SMILES Code :	O=CC1=CC(Br)=CN=C1OC
MDL No. :	MFCD05663521
InChI Key :	VRNOWEKCASDTFG-UHFFFAOYSA-N
Pubchem ID :	1516403

Safety of [ 103058-87-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 103058-87-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	43.82
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	39.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.93
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.31
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.67
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.68
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.16
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.28
Solubility	1.14 mg/ml ; 0.00529 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.73
Solubility	3.99 mg/ml ; 0.0185 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.96
Solubility	0.237 mg/ml ; 0.0011 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.69 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.77

Application In Synthesis of [ 103058-87-3 ]

* 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 [ 103058-87-3 ]

[ 103058-87-3 ] Synthesis Path-Downstream 1~35

1
[ 99-91-2 ]
[ 103058-87-3 ]
[ 103058-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In tetrahydrofuran; methanol; water;	EXAMPLE 7 To a solution of 6.5 g of <strong>[103058-87-3]5-bromo-2-methoxypyridine-3-carboxaldehyde</strong> in 30 ml of tetrahydrofuran under nitrogen was added 200 ml of methanol followed by 4.6 g of 4-chloroacetophenone. Then, a solution of 6.6 g of 85% potassium hydroxide in 15 ml of water was added. The mixture warmed, became yellow, and deposited a thick precipitate. It was then stirred mechanically for about 1.5 hours until the temperature fell back to about 25 C. It was then further cooled in an ice bath and neutralized by the addition of 20 ml of aqueous 5M hydrochloric aid in small portions. The resulting pasty mixture was poured into 400 ml of water, acidified to a pH of 1 with aqueous 1N hydrochloric acid and then filtered. The moist product was boiled with 2-propanol/ethyl acetate (3:1), cooled and filtered. The filter cake was dried under reduced pressure to give (E)-3-(5-bromo-2-methoxy-3-pyridinyl)-1-(4-chlorophenyl)-2-propen-1-one as a pale yellow solid melting at about 168.5-171.5 C.

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.
[2]Patent: US4588733,1986,A .

2
[ 13472-60-1 ]
[ 68-12-2 ]
[ 65873-73-6 ]
[ 103058-87-3 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

3
[ 103058-87-3 ]
[ 122-00-9 ]
[ 106585-02-8 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

4
[ 103058-87-3 ]
[ 2642-63-9 ]
[ 103058-90-8 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

5
[ 103058-87-3 ]
[ 41295-20-9 ]
[ 1020104-83-9 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[103058-87-3]5-bromo-2-methoxy-pyridine-3-carbaldehyde</strong> (0.87 g, 4.03 mmol) in dry MeOH (15 mL) was treated with 4-p-tolyloxy-phenylamine (0.88 g, 4.43 mmol) and reflux for 2.5 h. The solution was cooled to 0 C. and treated slowly with NaBH4 (0.38 g, 10.1 mmol). The reaction stirred at room temperature overnight. Additional NaBH4 (0.38 g, 10.1 mmol) was added and the reaction was continued stirring for additional 6 h. The solvent was removed and the residue was partitioned between CH2Cl2 (20 mL) and water (10 mL). The organic portion was brought to the usual work-up to give a crude material. The product was yielded after chromatography purification (silica gel, 25% EtOAc/hexanes). MS (EI) 399, 401 (M+H)+.

References: [1]Patent: US2008/103129,2008,A1 .Location in patent: Page/Page column 50.

6
[ 1628-89-3 ]
[ 103058-87-3 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

7
[ 103058-87-3 ]
[ 102830-89-7 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

8
[ 103058-87-3 ]
[ 102830-66-0 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

9
[ 103058-87-3 ]
(E)-3-(5-Bromo-2-methoxy-pyridin-3-yl)-1-p-tolyl-prop-2-en-1-ol [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

10
[ 103058-87-3 ]
[ 102830-72-8 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

11
[ 103058-87-3 ]
[ 102830-82-0 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

12
[ 103058-87-3 ]
[ 102830-84-2 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

13
[ 103058-87-3 ]
[ 103059-00-3 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

14
[ 103058-87-3 ]
[ 102830-64-8 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

15
[ 103058-87-3 ]
[ 103058-91-9 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

16
[ 103058-87-3 ]
[ 102830-74-0 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

17
[ 103058-87-3 ]
[ 102830-69-3 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

18
[ 103058-87-3 ]
[ 102830-70-6 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

19
[ 103058-87-3 ]
[ 102830-73-9 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

20
[ 103058-87-3 ]
[ 103080-28-0 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1583 - 1592.

21
[ 103058-87-3 ]
[ 865156-70-3 ]

Yield	Reaction Conditions	Operation in experiment
		a) 5-Bromo-2-methoxv-3- (4-methoxv-but-1 (E, Z)-envl)-pyridine; 2.45 mi of a 1 M solution of sodium-bis (trimethylsilyl) amide in tetrahydrofuran are added. to a suspension of 2.4 mmol (3-methoxy-propyl)-triphenyl-phosphonium bromide [111088-69-8] in 8 ml tetrahydrofuran unter an argon atmosphere at 0C. The reaction mixture is stirred for 30 minutes at 0C and then 1.6 mmol <strong>[103058-87-3]5-bromo-2-methoxy-pyridine-3-carbaldehyde</strong> [103058-87- 3] are added. The reaction mixture is warmed to room temperature and then diluted with tert- butyl methyl ether. The solution is washed with saturated aqueous sodium hydrogen- carbonate solution. The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (Si02 60F) and identified based on its Rf value.
		n-Butyllithium (120 ml, 1.6M in hexane) is added to a suspension of 80.74 g of (3-methoxy- propyl)triphenylphosphonium bromide [11 1088-69-8] in 250 ml of tetrahydrofuran under an argon atmosphere at 0C. The reaction mixture is stirred at 0C for 50 minutes and then 28 g of <strong>[103058-87-3]5-bromo-2-methoxypyridine-3-carbaldehyde</strong> [103058-87-3] are added. The reaction mixture is stirred at 0C for 1 hour and then at room temperature for 1 hour and diluted with tert-butyl methyl ether. The solution is washed with 1 M sodium bicarbonate solution. The organic phase is dried over sodium sulphate and evaporated. The title compound is obtained as a yellowish oil from the residue by flash chromatography (SiO2 60F). Rt = 5.03 (Gradient I)

References: [1]Patent: WO2005/90305,2005,A1 .Location in patent: Page/Page column 35-36.
[2]Patent: WO2007/31558,2007,A1 .Location in patent: Page/Page column 29.

22
[ 59-48-3 ]
[ 103058-87-3 ]
[ 928777-16-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With piperidine; In ethanol; at 80℃; for 2h;	3- ( (5-bromo-2-methoxypyridin-3-yl)methylene) indolin-2-one EPO <DP n="53"/>[00119] To a solution of indolinone (130mg, 0.98mmol) in ethanol (5mL) was added 5-bromo-2-methoxypyridine-3- carbaldehyde (J. net. Chem, 1985, (22), 1583-1592) (200mg, 0.98mmol, leq) , followed by piperidine (0.194mL, 1.9mmol, 2eq) . The reaction mixture was heated at 8O0C for 2 hours and then allowed to cool to room temperature. The precipitate that formed was collected by filtration and washed with ethanol to give the title compound (180mg, 55%;

References: [1]Patent: WO2007/27528,2007,A2 .Location in patent: Page/Page column 51-52.

23
[ 928777-12-2 ]
[ 103058-87-3 ]
[ 928777-13-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 3.58333h;	To 5-bromo~2-methoxypyridine-3-carbaldehyde {1.5 g, 6.95 mmol) and diethyl (4- (4- ( fcert-butoxycarbonyl)piperazin- 1-yl) phenyl )methylphosphonate (2.39 g, 5.79 mmol) in anhydrous THF (50 mL) under nitrogen was added potassium tert-butoxide (1.30 g, 11.6 mmol) at rt over 5 min. After 3 h a further portion of the aldehyde (160 ialphag, 0.74 mmol) was added. After a further 30 min the reaction was concentrated and the residue purified by column chromatography (30% EtOAc in PE) to give the title compound (2.27 g, 83%) as a yellow oil. 1H NMR (CDCl3) 1.51 (9H, s), 3.24 (4H, t) , 3.68 (4H, t), 4.00 (3H, s), 7.02 (2H, d) , 7.11 (2H, m) , 7.49 (2H, d) , 7.89 (IH, s) , 8.07 (IH, s) .

References: [1]Patent: WO2007/27528,2007,A2 .Location in patent: Page/Page column 48-49.

24
[ 103058-87-3 ]
[ 126747-14-6 ]
4-(5-formyl-6-methoxypyridin-3-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 12h;Heating / reflux;	Reference Example 1; 4- (5-formgammal-6-methoxypyridin-3-gammal) benzonitrile; A mixture of <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (2.0 g) synthesized by a known method (Journal of Heterocyclic Chemistry 1985, 22(6), 1583-1592), (4- cyanophenyl) boronic acid (1.36 g) , Pd(PPh3)4 (0.32 g) and potassium carbonate (2.6 g) in THF (20 mL) and water (10 mL) was heated under reflux for 12 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated under reduced pressure. The obtained residue was crystallized from acetone/ethanol/IPE to give the title compound (0.93 g) as white crystals . melting point: 157C

References: [1]Patent: WO2007/89031,2007,A1 .Location in patent: Page/Page column 80-81.

25
[ 103058-87-3 ]
[ 111088-69-8 ]
[ 865156-70-3 ]

Yield	Reaction Conditions	Operation in experiment
		a) 5-Bromo-2-methoxv-3- (4-methoxv-but-1 (E, Z)-envl)-pvridine; 2. 45 ml of a 1M solution of sodium-bis(trimethylsilyl) amide in tetrahydrofuran are added. to a suspension of 2. 4 mmol (3-methoxy-propyl)-triphenyl-phosphonium bromide [111088-69-8] in 8 mi tetrahydrofuran unter an argon atmosphere at 0C. The reaction mixture is stirred for 30 minutes at 0C and then 1. 6 mmol <strong>[103058-87-3]5-bromo-2-methoxy-pyridine-3-carbaldehyde</strong> [103058-87- 3] are added. The reaction mixture is warmed to room temperature and then diluted with tert- butyl methyl ether. The solution is washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value

References: [1]Patent: WO2005/90304,2005,A1 .Location in patent: Page/Page column 44.

26
[ 1185288-83-8 ]
[ 103058-87-3 ]
[ 1185288-88-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4406 - 4409.

27
[ 103058-87-3 ]
[ 1254123-51-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 25℃; for 72h;Inert atmosphere;	Example 22i 5-Bromo-3-(difluoromethyl)-2-methoxypyridine To <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (5 g, 23 mmol) in dry CH2Cl2 (100 mL) at 0 C. under argon was diethylaminosulphur trifluoride (3.69 mL, 30.1 mmol) added over 1 min. The reaction mixture was stirred for three days while the reaction warmed to r.t. The reaction was quenched by the addition of sat. aqueous sodium bicarbonate solution. The reaction mixture was combined with another reaction based on <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (100 mg, 0.46 mmol) prior to workup. The phases were separated and the water phase was further extracted with CH2Cl2 (x 3). The organic layers were pooled, dried (Na2SO4), filtered and concentrated to give the title compound (5.71 g, quant. yield): 1H NMR (400 MHz, DMSO-d6) delta ppm 3.94 (s, 3H), 7.04 (t, 1 H), 8.10-8.16 (m, 1H), 8.48 (m, 1H); MS (ES+) m/z 238 [M+H]+.
100%	With diethylamino-sulfur trifluoride; In dichloromethane; at 0℃; for 48h;	To a mixture of <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (10.0 g, 46.3 mmol) in dry DCM (100 mL) under N2 at 0 C. was added DAST (29.8 g, 185.2 mmol) and stirred at 0 C. for 2 days. The reaction was quenched with 100 mL of a saturated NaHCO3 solution. The aqueous layer was extracted with DCM (100 mL*3). The combined organic layers were washed with NaHCO3 (sat, 100 mL) and brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 5-bromo-3-(difluoromethyl)-2-methoxypyridine as a yellow oil (11.0 g). Yield 100% (ESI 238.1 (M+H)+).

References: [1]Patent: US2012/165346,2012,A1 .Location in patent: Page/Page column 18.
[2]Patent: US2019/315692,2019,A1 .Location in patent: Paragraph 0228; 1120; 1121.

28
[ 103058-87-3 ]
[ 1383847-34-4 ]

References: [1]Patent: US2012/165346,2012,A1 .

29
[ 41838-46-4 ]
[ 103058-87-3 ]
N-((5-bromo-2-methoxypyridin-3-yl)methyl)-1-methylpiperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium cyanoborohydride; acetic acid; In methanol; at 20℃; for 22h;	5-Bromo-2-methoxynicotinaldehyde (472 mg, 2.18 mmol) and 1-methylpiperidin-4- amine (249 mg, 2.18 mmol) were stirred in methanol (10 mL). Acetic acid (0.12 mL) and sodium cyanoborohydride (137 mg, 2.18 mmol) were then added and the mixturewas stirred at room temperature for 22 h. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between dichloromethane and a saturated aqueous sodium hydrogen carbonate solution. The phases were separated. The aqueous layer was extracted with dichloromethane. The combined organics were dried over anhydrous magnesium sulphate, filtered and evaporated under reducedpressure to give 647 mg (94% yield) of the title compound.LRMS (M+1): 314, 3161H NMR (400 MHz, Chloroform-d) 6 ppm 1.44 (2H, m), 1.88 (2H, m), 2.26 (3H, s), 2.43(1 H, m), 2.81 (2H, m), 3.73 (2H, s), 3.93 (3H, s), 7.69 (1 H, d, J = 2.4 Hz), 8.08 (1 H, d, J= 2.4 Hz)

References: [1]Patent: WO2015/91532,2015,A1 .Location in patent: Page/Page column 86.

30
[ 41838-46-4 ]
[ 103058-87-3 ]
tert-butyl((5-bromo-2-methoxypyridin-3-yl)methyl)(1-methylpiperidin-4-yl)carbamate [ No CAS ]

References: [1]Patent: WO2015/91532,2015,A1 .

31
[ 4009-98-7 ]
[ 103058-87-3 ]
5-bromo-2-methoxy-3-(2-methoxyvinyl)pyridine [ No CAS ]
5-bromo-2-methoxy-3-(2-methoxyvinyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 : To a solution of (methoxymethyl)triphenylphosphonium chloride (1.5 equiv.) in THF (0.3 M) at 0 C was added NaHMDS (1M in THF, 1.55 equiv.) and the red solution was stirred in the cold bath for 30 min at which point 5-bromo-2- methoxynicotinaldehyde (1.0 equiv.) was added. After stirring in the cold bash for 30 min, the solution was allowed to warm to rt, stirred for 2 hours, then partitioned between ethyl acetate and sat. sodium bicarbonate. The layers were mixed, separated, the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified via siiica gel chromatography (0-30% ethyl aeetate/n-heptanes) to yield 5-bromo-2- methoxy-3-(2-methoxyvinyl)pyridine contaminated with the starting aldehyde. This mixture was dissolved in methanol and 0.5 equiv. of sodium borohydride were added. After stirring at rt for 10 min, the volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated. Purification via silica gel chromatography (ISCO, 0-15% ethyl acetate/n- heptanes) afforded 5-bromo-2-methoxy-3-(2-methoxyvinyl)pyridine in 11% yield as a mixture of enol ethers isomers. LCMS (m/z) (M+H) - 244.0/246.0, Rt = 0.97 and 1.01 min.

References: [1]Patent: WO2016/38582,2016,A1 .Location in patent: Paragraph 00161.

32
(2S,3S,4S,5S)-tert-butyl 4-amino-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
[ 103058-87-3 ]
(2S,3S,4S,5S)-tert-butyl 4-(((5-bromo-2-methoxypyridin-3-yl)methyl)amino)-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5-Bromo-2-methoxynicotinaldehyde (0.529 g, 2.450 mmol) and (2S,3S,4S,5S)-tert-butyl 4-amino-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate (Example 25B, 1 g, 2.333 mmol) were mixed in methanol (12 mL), and the reaction was stirred at room temperature for 1 hour. Sodium cyanoborohydride (0.740 g, 11.78 mmol) was then added in one portion, and the reaction continued to stir at room temperature for 1.5 days. After this time, the solvent was removed in vacuo, and the residue was taken up in 100 mL water and 100 mL CH2Cl2 and transferred to a separatory funnel. The separatory funnel was shaken, the phases were separated, and the aqueous layer was extracted twice more with CH2Cl2 (100 mL each time). The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography, eluting with 5 to 30% ethyl acetate-heptanes, provided the impure title compound, 1.02 g. The material was taken directly into the next reaction without additional purification. 1H NMR (400 MHz, dimethyl sulfoxide-d6) delta ppm 8.00 (m, 1H), 7.59 (m, 2H), 7.40-7.19 (m, 4H), 5.17 (d, J=6.9 Hz, 1H), 4.40 (d, J=2.7 Hz, 1H), 3.68 (s, 3H), 3.41-3.21 (m, 3H), 2.26 (m, 1H), 2.19 (m, 1H), 1.68-1.02 (m, 10H), 1.43 (s, 9H), 0.98 (s, 9H); MS (ESI+) m/z 628.0 (M+H)+.

References: [1]Patent: US2018/99931,2018,A1 .Location in patent: Paragraph 2261.

33
[ 103058-87-3 ]
(2S,3S,4S,5S)-3-tert-butyl-1-(cyclohexanecarbonyl)-4-[(2-methoxy-5-phenylpyridin-3-yl)methyl]amino}-5-phenylpyrrolidine-2-carboxylic acid [ No CAS ]

References: [1]Patent: US2018/99931,2018,A1 .

34
[ 103058-87-3 ]
(2S,3S,4S,5S)-tert-butyl 3-(tert-butyl)-1-(cyclohexanecarbonyl)-4-(((2-methoxy-5-phenylpyridin-3-yl)methyl)amino)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]

References: [1]Patent: US2018/99931,2018,A1 .

35
[ 103058-87-3 ]
(2S,3S,4S,5S)-3-tert-butyl-4-[(5-tert-butyl-2-methoxypyridin-3-yl)methyl]amino}-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylic acid trifluoroacetic acid [ No CAS ]

References: [1]Patent: US2018/99931,2018,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions of Ethers • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 103058-87-3 ]

Bromides

A514770 [760207-87-2]

5-Bromo-2-methoxy-3-methylpyridine

Similarity: 0.92

A156071 [1256811-02-5]

1-(5-Bromo-2-methoxypyridin-3-yl)ethanone

Similarity: 0.88

A109888 [13472-85-0]

5-Bromo-2-methoxypyridine

Similarity: 0.83

A252192 [870521-31-6]

5-Bromo-2-isopropoxypyridine

Similarity: 0.83

A428862 [83664-33-9]

2-(Benzyloxy)-5-bromopyridine

Similarity: 0.82

Aldehydes

A177525 [269058-49-3]

3-Bromo-6-methoxypicolinaldehyde

Similarity: 0.74

A110184 [70201-43-3]

3-Bromoisonicotinaldehyde

Similarity: 0.67

A111333 [65873-72-5]

6-Methoxynicotinaldehyde

Similarity: 0.67

A180879 [635712-99-1]

6-(Benzyloxy)nicotinaldehyde

Similarity: 0.67

A127645 [1005772-69-9]

1-Methoxy-4-isoquinolinecarboxaldehyde

Similarity: 0.66

Ethers

A514770 [760207-87-2]

5-Bromo-2-methoxy-3-methylpyridine

Similarity: 0.92

A156071 [1256811-02-5]

1-(5-Bromo-2-methoxypyridin-3-yl)ethanone

Similarity: 0.88

A109888 [13472-85-0]

5-Bromo-2-methoxypyridine

Similarity: 0.83

A252192 [870521-31-6]

5-Bromo-2-isopropoxypyridine

Similarity: 0.83

A428862 [83664-33-9]

2-(Benzyloxy)-5-bromopyridine

Similarity: 0.82

Related Parent Nucleus of
[ 103058-87-3 ]

Pyridines

A514770 [760207-87-2]

5-Bromo-2-methoxy-3-methylpyridine

Similarity: 0.92

A156071 [1256811-02-5]

1-(5-Bromo-2-methoxypyridin-3-yl)ethanone

Similarity: 0.88

A109888 [13472-85-0]

5-Bromo-2-methoxypyridine

Similarity: 0.83

A252192 [870521-31-6]

5-Bromo-2-isopropoxypyridine

Similarity: 0.83

A428862 [83664-33-9]

2-(Benzyloxy)-5-bromopyridine

Similarity: 0.82

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CAS No.: 103058-87-3

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CAS No.: 103058-87-3

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CAS No.: 103058-87-3

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CAS No.: 103058-87-3

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Physicochemical Properties

Lipophilicity

Water Solubility

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Medicinal Chemistry

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[ 103058-87-3 ] Synthesis Path-Downstream 1~35

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Bromides

Aldehydes

Ethers

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Pyridines

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