1-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-ol → 1-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-one

HRID 1295877

Reaction equation

HRID 1295877 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:19]([OH:22])[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:19](=[O:22])[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 179681531-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-ol

Product 1

HCID 112321611-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-alpha]pyridin-3-yl]-2-propyn-1-oneYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-ol (870 mg, 2.78 mmol) in dichloromethane (150 mL) was added manganese dioxide (9.6 g, 111 mmol) and the resulting suspension was stirred at room temperature for 1.5 hours. The mixture was filtered through Celite. The filtrate was concentrated in vacuo to give 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (680 mg, 78%) as a golden foam. 1H NMR (CDCl3): δ 9.66 (d, 1 H), 7.65 (d, 1 H), 7.34 (t, 1 H), 7.28–7.22 (m, 2 H), 7.10 (t, 1 H), 7.02 (m, 1 H), 3.86 (s, 3 H), 2.86 (s, 1 H); MS m/z 311 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cb086665708042fb88e8bf0819bf558f
Source dataset
uspto-grants-2007_07
Patent number
US07244740B2

Linked notes

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