6-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde → 6-(5-Fluoropyridin-3-yl) imidazo[1,2-a]pyridine-3-carbaldehyde

HRID 401456Notes

Reaction equation

HRID 401456 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[N:18][CH:19]=1>>[F:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=3)[CH:7]=2)[CH:17]=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 213456766-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde2×HCID 44717403(5-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 866706046-(5-Fluoropyridin-3-yl) imidazo[1,2-a]pyridine-3-carbaldehydeYield 52%

Procedure

The title compound was prepared by following the procedure as described for Intermediate 1 using 6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde and 5-fluoropyridin-3-ylboronic acid. Yield: 52%; 1H NMR (DMSO-d6; 300 MHz): δ 10.01 (s, 1H), 9.66 (s, 1H), 8.84 (s, 1H), 8.66-8.67 (d, 1H, J=2.1 Hz), 8.59 (s, 1H), 8.18-8.21 (d, 1H, J=9 Hz), 8.08-8.11 (d, 1H, J=9.6 Hz), 8.03 (s, 1H); MS: m/z 241.6 (M+1)+.

Sources & evidence

ORD record
ord-1d7b034eeca742a7b101375cc0ab8683
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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