Ethane, 2-bromo-1,1-diethoxy- → 8-Bromo-6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine

HRID 1293735Notes

Reaction equation

HRID 1293735 reaction equation
[Br:1][C:2]1[C:3]([NH2:15])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:7]=1.[CH2:16](OC(OCC)CBr)[CH3:17]>>[Br:1][C:2]1[C:3]2[N:4]([CH:16]=[CH:17][N:15]=2)[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 580678233-Bromo-5-(4-chlorophenyl)pyridin-2-amine

Product 1

HCID 670008688-Bromo-6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine

Procedure

Prepared from crude 3-bromo-5-(4-chloro-phenyl)-pyridin-2-ylamine (example C.27 step 2) (ca. 50 mmol) and bromoacetaldehyde diethyl acetal (90%, 17.2 mL, 100 mmol) as described in example C.20 step 1. Obtained the pure 8-bromo-6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine after chromatography as a light brown solid (11.91 g, 77%). MS (ISP) 307.1 [(M+H)+], 309.1 [(M+2+H)+], 311.1 [(M+4+H)+].

Sources & evidence

ORD record
ord-27a7b821d8fd47e1b50a4bbc327a8ff4
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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