Potassium Bromide → 3-Bromoimidazo[1,2-a]pyridine-8-carbaldehyde

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=12.[K+].[Br-:13]>>[Br:13][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]2=[N:1][CH:2]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 10997174Imidazo(1,2-a)pyridine-8-carbaldehyde

Product 1

HCID 462060573-Bromoimidazo[1,2-a]pyridine-8-carbaldehyde

Procedure

From 4a (yield: 35%); mp 104-106° C.; IR (KBr) 1694, 1186 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.09 (t, 1H J=7 Hz), 7.74 (s, 1H), 7.86 (d, 1H, J=7 Hz), 8.32 (d, 1H, J=7 Hz), 10.66 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 96.4, 112.9, 124.2, 127.1, 128.5, 134.6, 144.2, 188.2; MS m/z 226 (M++2, 45), 224 (M+, 46), 198 (99), 196 (100), 117 (76), 90 (54), 63 (30).

Sources & evidence

ORD record: ord-30dbd52d43504c6c8135ce101a531ee4
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404707B2

Reaction notes

Loading…