Potassium Bromide → Imidazo(1,2-a)pyridine-8-carbaldehyde

HRID 1951327Notes

Reaction equation

HRID 1951327 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[N:5]([CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[K+].[Br-]>>[N:11]1[CH:10]=[CH:9][N:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH:2]=[O:1])[C:4]=12

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 11029987Imidazo[1,2-a]pyridin-8-ylmethanol

Product 1

HCID 10997174Imidazo(1,2-a)pyridine-8-carbaldehydeYield 85%

Procedure

From 3a, reaction time 1.5 h (yield: 85%); mp 137-139° C. (in Yamanaka, M. and al. Chem. Pharm. Bull. 1991, 39, 1556-1567: 103-104° C.); IR (KBr) 1675, 1450, 1320, 1175 cm−1, 1H NMR (400 MHz, CDCl3) δ 7.01 (t, 1H, J=6.5 Hz), 7.75 (s, 1H), 7.82 (s, 1H), 7.86 (d, 1H, J=6.5 Hz), 8.42 (d, 1H, J=6.5 Hz), 10.8 (s, 1H); 13C NMR (CDCl3) δ 111.9, 113.3, 124.2, 126.9, 130.7, 134.9, 143.8, 188.9.

Workup

  1. custommp 137-139° C. (in Yamanaka, M. and al. Chem. Pharm. Bull. 1991, 39, 1556-1567: 103-104° C.)

Sources & evidence

ORD record
ord-940b9fd095c747dcb937e49e196c590d
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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