Potassium Bromide → 2-(1-Methylethyl)imidazo[1,2-a]pyridine-8-carboxaldehyde

HRID 1951332Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:4]2[N:5]([CH:9]=[C:10]([CH:12]([CH3:14])[CH3:13])[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[K+].[Br-]>>[CH:12]([C:10]1[N:11]=[C:4]2[C:3]([CH:2]=[O:1])=[CH:8][CH:7]=[CH:6][N:5]2[CH:9]=1)([CH3:14])[CH3:13]

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 46205730HCID 46205730, compound

Product 1

HCID 462060552-(1-Methylethyl)imidazo[1,2-a]pyridine-8-carboxaldehydeYield 57%

Procedure

From 3f: reaction time 15 h (yield: 57%); mp 70-72° C.; IR (KBr) 1669, 1540, 1500 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.39 (d, 6H, J=7 Hz), 3.20 (sept, 1H, J=7 Hz), 6.90 (t, 1H, J=7 Hz), 7.46 (s, 1H), 7.77 (d, 1H, J=7 Hz), 8.30 (d, 1H, J=7 Hz), 10.79 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 22.4, 28.6, 107.9, 111.2, 123.4, 125.5, 130.2, 143.7, 156.0, 189.2; MS m/z 188 (M+, 60), 173 (56), 160 (100), 145 (26), 78 (21).

Sources & evidence

ORD record: ord-d68737e8b3b24db094fba638f5f72b0c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404707B2

Reaction notes

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