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

HRID 1951338Notes

Reaction equation

HRID 1951338 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=O)[C:5]=12.[K+].[Br-]>>[CH3:10][C:6]1[C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 10997174Imidazo(1,2-a)pyridine-8-carbaldehyde

Product 1

HCID 3279578-Methylimidazo(1,2-a)pyridineYield 10%

Procedure

From 4a (yield: 10%); mp: 150-152° C.; IR (KBr) 2100, 1700, 1600, 1280 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.41 (t, 3H, J=7 Hz), 4.39 (q, 2H, J=7 Hz), 6.83 (t, 1H, J=7 Hz), 7.57 (d, 1H, J=1 Hz), 7.61 (d, 1H, J=1 Hz), 7.76 (s, 1H), 8.06 (dd, 1H, J=7, 1 Hz), 8.17 (dd, 1H, J=7, 1 Hz). MS m/z 257 (M+, 1), 229 (61), 183 (100), 155 (31), 129 (23), 104 (14). Further elution gave 8-methylimidazo[1,2-a]pyridine (yield: 10%-Kaiser, C. and al. J. Med. Chem. 1992, 35, 4415-4424).

Workup

  1. washFurther elution

Sources & evidence

ORD record
ord-5b8d08964e30434c92afac73cc8daf5f
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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