3-Bromo-4-methylpyridin-2-amine → HCID 58056736, compound

HRID 561057

Reaction equation

HRID 561057 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=O)[CH2:17]Br)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[C:26]([Br:27])=[C:25]([CH3:28])[CH:24]=[CH:23][N:22]=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:20]=[C:21]2[C:26]([Br:27])=[C:25]([CH3:28])[CH:24]=[CH:23][N:22]2[CH:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 144180433-Bromo-4-methylpyridin-2-amineHCID 54423887HCID 54423887, compound

Product 1

HCID 58056736HCID 58056736, compoundYield 47.2%

Procedure

Following the procedures of example 14, (S)-benzyl-2-(2-bromoacetyl)pyrrolidine-1-carboxylate (0.400 g, 1.23 mmol) and 2-amino-3-bromo-4-methylpyridine (0.2344 g, 1.25 mmol), produced the crude material which was adsorbed onto silica gel and purified by flash chromatography (12 g SiO2, 0-50% ethyl acetate in hexanes) to give (S)-benzyl-2-(8-bromo-7-methylimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.239 g, 0.58 mmol, 47%).

Workup

  1. customproduced the crude material which
  2. custompurified by flash chromatography (12 g SiO2, 0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6209c2edc8e54238826cba538eaa7e5c
Source dataset
uspto-grants-2011_11
Patent number
US08063218B2

Linked notes

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