Dimethylformamide → HCID 82060381, compound

HRID 456706Notes

Reaction equation

HRID 456706 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl: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]>>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:18])[C:5]2[N:6]([C:8]([CH:26]=[O:27])=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 4259053HCID 4259053, compound

Product 1

HCID 82060381HCID 82060381, compoundYield 75%

Procedure

6,8-Dichloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridine (6 g, 0.021 moles) was treated with phosphorous oxychloride (3.0 mL, 33 mmol) in N,N-dimethylformamide in a similar manner as described in Example 2 to give 6,8-dichloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridine-3-carbaldehyde (4.9 g, 75%) as a white solid. 1H NMR (CDCl3): δ 10.05 (s, 1H), 9.69 (d, 1H), 7.86 (q, 2H), 7.65 (d, 1H), 7.25 (t, 2H); 19F NMR (CDCl3) δ −110.3; MS m/z 309 (M+1).

Sources & evidence

ORD record
ord-ad8831d808c04a07ad043c0486f8270e
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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