Sodium hydride → 2-{4-[(E)-2-(2-methoxy-4-nitrophenyl)ethenyl]phenyl}-6-methylimidazo[1,2-a]pyridine

HRID 339597Notes

Reaction equation

HRID 339597 reaction equation
[H-].[Na+].P(=O)([O-])O[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]3[CH:21]=2)=[CH:8][CH:7]=1.[CH3:24][O:25][C:26]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:27]=1[CH:28]=O.C(Cl)Cl.CO>C1COCC1>[CH3:24][O:25][C:26]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:27]=1/[CH:28]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]3[CH:21]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27595992-Methoxy-4-nitrobenzaldehydeHCID 21226129Dichloromethane methanolHCID 178423143HCID 178423143, compound

Product 1

HCID 673129292-{4-[(E)-2-(2-methoxy-4-nitrophenyl)ethenyl]phenyl}-6-methylimidazo[1,2-a]pyridineYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in the Alkene Formation section using sodium hydride (60% dispersion in mineral oil, 33 mg, 0.838 mmol), diethyl[4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl phosphonate (250 mg, 0.698 mmol) and 2-methoxy-4-nitrobenzaldehyde (126 mg, 0.698 mmol) in dry THF (15 ml) to give the title compound (199 mg, 74%) as an orange solid after work-up and flash chromatography (25:1 DCM/MeOH).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d2fb2abc4f6e465f81ff44c59fa81da9
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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