6-Fluoroimidazo[1,2-a]pyridine-2-carboxylic acid → 5-Methylimidazo[1,2-a]pyridine-2-carboxylic acid

HRID 1293549Notes

Reaction equation

HRID 1293549 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=2)[CH:7]=1.[CH2:14]([O:16][C:17]([C:19]1[NH:20][CH:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]2[CH:28]=1)=[O:18])[CH3:15]>>[CH3:27][C:23]1[N:22]2[CH:28]=[C:19]([C:17]([OH:18])=[O:16])[N:20]=[C:21]2[CH:26]=[CH:25][CH:24]=1.[CH3:14][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=2)[CH:7]=1.[CH2:14]([O:16][C:17]([C:19]1[N:20]=[C:21]2[CH:26]=[CH:25][C:24]([CH3:2])=[CH:23][N:22]2[CH:28]=1)=[O:18])[CH3:15]

Participants

5

Reactant 2

HCID 223975086-Fluoroimidazo[1,2-a]pyridine-2-carboxylic acid2×HCID 694322985-Methyl-1,8a-dihydro-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester

Product 3

HCID 20621695-Methylimidazo[1,2-a]pyridine-2-carboxylic acidHCID 27598636-Methylimidazo[1,2-a]pyridine-2-carboxylic acidHCID 12558372Ethyl 6-methylimidazo(1,2-a)pyridine-2-carboxylate

Procedure

5-Methyl-imidazo[1,2-a]pyridine-2-carboxylic acid was prepared in a similar manner to 6-fluoro-imidazo[1,2-a]pyridine-2-carboxylic acid (see Example 25) using the commercially available 5-methyl-1,8a-dihydro-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester. 6-Methyl-imidazo[1,2-a]pyridine-2-carboxylic acid and 6-methyl-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester were prepared in a similar manner to 6-fluoro-imidazo[1,2-a]pyridine-2-carboxylic acid and its ester above.

Sources & evidence

ORD record
ord-234caf707cb74005af7652ee21c87dcc
Source dataset
uspto-grants-2007_07
Patent number
US07238811B2

Reaction notes

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