Sodium hydride → 2-(4-{(e)-2-[4-Nitro-2-(2-fluoroethoxy)phenyl]ethenyl}phenyl)-6-methylimidazo[1,2-a]pyridine

HRID 339598Notes

Reaction equation

HRID 339598 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.[F:24][CH2:25][CH2:26][O:27][C:28]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:29]=1[CH:30]=O.C(Cl)Cl.CO>C1COCC1>[N+:36]([C:34]1[CH:33]=[CH:32][C:29](/[CH:30]=[CH:5]/[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]4[CH:21]=3)=[CH:8][CH:7]=2)=[C:28]([O:27][CH2:26][CH2:25][F:24])[CH:35]=1)([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 21226129Dichloromethane methanolHCID 583420152-(2-Fluoroethoxy)-4-nitrobenzaldehydeHCID 178423143HCID 178423143, compound

Product 1

HCID 583420032-(4-{(e)-2-[4-Nitro-2-(2-fluoroethoxy)phenyl]ethenyl}phenyl)-6-methylimidazo[1,2-a]pyridineYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in the Alkene Formation section using sodium hydride (60% dispersion in mineral oil, 27 mg, 0.67 mmol), diethyl[4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl phosphonate (200 mg, 0.559 mmol) and 2-(2-fluoroethoxy)-4-nitrobenzaldehyde (119 mg, 0.559 mmol) in dry THF (15 ml) to give the title compound (174 mg, 74%) as an orange solid after work-up and flash chromatography (50:1 DCM/MeOH).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-96afd8f593224df7ba715eec8fd54cb2
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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