4-Nitrobenzaldehyde → 6-Methyl-2-{4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl}imidazo[1,2-a]pyridine

HRID 339596Notes

Reaction equation

HRID 339596 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.[N+:24]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)([O-:26])=[O:25].C(Cl)Cl.CO>C1COCC1>[CH3:20][C:17]1[CH:18]=[CH:19][C:14]2[N:15]([CH:21]=[C:12]([C:9]3[CH:10]=[CH:11][C:6](/[CH:5]=[CH:31]/[C:30]4[CH:33]=[CH:34][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=4)=[CH:7][CH:8]=3)[N:13]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 24758Sodium hydrideHCID 21226129Dichloromethane methanolHCID 178423143HCID 178423143, compound

Product 1

HCID 451375946-Methyl-2-{4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl}imidazo[1,2-a]pyridineYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in the Alkene Formation section using sodium hydride (60% dispersion in mineral oil, 7 mg, 0.307 mmol), diethyl[4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl phosphonate (100 mg, 0.279 mmol) and 4-nitrobenzaldehyde (42 mg, 0.279 mmol) in THF (5 ml) to give the title compound (24 mg, 24%) as a yellow solid after work-up and flash chromatography (100:1 DCM/MeOH).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-434523b2c3424786a2b627a1a79b10d2
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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