Imidazo[1,2-a]pyridine-8-carboxylic acid, 2-methyl-, ethyl ester → 2-Methylimidazo[1,2-a]pyridine-8-methanol

HRID 1951320Notes

Reaction equation

HRID 1951320 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=[CH:6][N:5]2[CH:15]=1>C(Cl)(Cl)(Cl)Cl>[OH:11][CH2:10][C:9]1[C:4]2[N:5]([CH:15]=[C:2]([CH3:1])[N:3]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 18983836Imidazo[1,2-a]pyridine-8-carboxylic acid, 2-methyl-, ethyl ester

Product 1

HCID 139003302-Methylimidazo[1,2-a]pyridine-8-methanol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

From 2b (yield: 42%) as an oil; IR (CCl4) 2960, 1499, 1366, 1324 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.36 (s, 3H), 4.96 (s, 2H), 6.64 (t, 1H, J=7 Hz), 7.11 (d, 1H, J=7 Hz), 7.25 (s, 1H), 7.88 (d, 1H, J=7 Hz); 13C NMR (100 MHz, CDCl3) δ 14.0, 60.8, 109.7, 111.9, 121.5, 124.1, 129.2, 142.2, 143.6; MS m/z 162 (M+, 36), 161 (100), 133 (55), 132 (46), 78 (31), 51 (16).

Sources & evidence

ORD record
ord-88d50f9d48964cd5ad66e3dbf8713ce3
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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