Dimethylformamide → HCID 2756999, compound

HRID 456711Notes

Reaction equation

HRID 456711 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][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:25]=[O:26]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:25]=[O:26])=[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 11804756-bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 2756999HCID 2756999, compound

Procedure

6-Bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridine (7 g, 0.024 moles) was treated with phosphorous oxychloride (3.4 mL, 36 mmol) in N,N-dimethylformamide in a similar manner as described in Example 2 to give, after recrystallization from acetonitrile, 6-bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde (6.12 g, 80%) as a white solid. 1H NMR (CDCl3): δ 10.08 (s, 1H), 9.88 (s, 1H), 7.86 (q, 2H), 7.72 (m, 2H), 7.28 (t, 2H); 19F NMR (CDCl3) δ −110.6; MS m/z 320 (M+1).

Workup

  1. customto give
  2. customafter recrystallization from acetonitrile, 6-bromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde (6.12 g, 80%) as a white solid

Sources & evidence

ORD record
ord-5fb1bb615f4847fd93bb93bc7cb6521c
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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