Dimethylformamide → HCID 18436710, compound

HRID 456709Notes

Reaction equation

HRID 456709 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:26]=[O:27]>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]2[N:6]([C:8]([CH:26]=[O:27])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 18436711HCID 18436711, compound

Product 1

HCID 18436710HCID 18436710, compoundYield 85%

Procedure

6-Bromo-2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridine (6 g, 0.021 moles) was treated was treated with phosphorous oxychloride (2.8 mL) in N,N-dimethylformamide in a similar manner as described in Example 2 to give 6-bromo-2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridine-3-carbaldehyde (5.7 g, 85%) as a white solid. 1H NMR (CDCl3): δ 10.04 (s, 1H), 9.73 (s, 1H), 7.86 (q, 2H), 7.53 (s, 1H), 7.25 (t, 2H), 2.75 (s, 3H); 19F NMR (CDCl3) δ −111.0; MS m/z 334 (M+1).

Sources & evidence

ORD record
ord-fc7b8193cd194e30ad8c03ceaeb928da
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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