Ethane, 2-bromo-1,1-diethoxy- → 6-Bromoimidazo[1,2-a]pyridine-8-carbonitrile

HRID 1293714Notes

Reaction equation

HRID 1293714 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11](OC(OCC)CBr)[CH3:12]>>[Br:10][C:7]1[CH:6]=[C:3]([C:4]#[N:5])[C:2]2[N:9]([CH:11]=[CH:12][N:1]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 242291992-Amino-5-bromopyridine-3-carbonitrile

Product 1

HCID 670011736-Bromoimidazo[1,2-a]pyridine-8-carbonitrileYield 32%

Procedure

Prepared from 2-amino-5-bromo-nicotinonitrile (example C.23 step 1) (26 g, 131 mmol) and bromoacetaldehyde diethyl acetal (90%, 45 mL, 263 mmol) as described in example C.20 step 1. Obtained the title compound as a light brown solid (9.3 g, 32%). MS (ISP) 222.1 [(M+H)+], 224 [(M+2+H)+].

Sources & evidence

ORD record
ord-fe88ea5346fa47d386612be35d6d5342
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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