Sodium hydride → 6-Methyl-2-(4-{(E)-2-[4-nitro-2-(2-tert-butyldimethylsiloxyethoxy)phenyl]ethenyl}phenyl)imidazo[1,2-a]pyridine

HRID 339595Notes

Reaction equation

HRID 339595 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]3[CH:27]=[CH:26][C:16]([CH2:17]P(=O)(OCC)OCC)=[CH:15][CH:14]=3)[N:12]=2)[CH:9]=1.[O:28]([CH2:36][CH2:37][O:38][C:39]1[CH:46]=[C:45]([N+:47]([O-:49])=[O:48])[CH:44]=[CH:43][C:40]=1[CH:41]=O)[Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].CCOC(C)=O.CCCCCC>C1COCC1>[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16](/[CH:17]=[CH:41]/[C:40]4[CH:43]=[CH:44][C:45]([N+:47]([O-:49])=[O:48])=[CH:46][C:39]=4[O:38][CH2:37][CH2:36][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[CH:26][CH:27]=3)[N:12]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 58342049Diethyl [4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl]phosphonateHCID 583422182-([2-Tert-butyldimethylsiloxy]ethoxy)-4-nitrobenzaldehyde

Product 1

HCID 583421826-Methyl-2-(4-{(E)-2-[4-nitro-2-(2-tert-butyldimethylsiloxyethoxy)phenyl]ethenyl}phenyl)imidazo[1,2-a]pyridineYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in the Alkene Formation section using sodium hydride (40 mg, 60% dispersion in mineral oil, 1.00 mmol), diethyl [4-(6-methylimidazo[1,2-a]pyridin-2-yl)benzyl]phosphonate (0.300 g, 0.837 mmol) and 2-([2-tert-butyldimethylsiloxy]ethoxy)-4-nitrobenzaldehyde (0.272 g, 0.837 mmol) in dry THF (30 ml) to give the title compound (0.285 g, 64%) as an orange solid after work-up and flash chromatography (2:1 EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-34e4cacbf17f4b96a7d239c465bd181b
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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