Sodium hydride → Ethyl 2-{(E)-2-[2-(cyclopentyloxy)-3-(difluoromethoxy)phenyl]vinyl}imidazo [1,2-a]pyridine-3-carboxylate

HRID 1882144Notes

Reaction equation

HRID 1882144 reaction equation
[CH:1]1([O:6][C:7]2[C:14]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-].[CH2:20]([O:22][C:23]([C:25]1[N:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]2=[N:27][C:26]=1[CH2:34][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:24])[CH3:21].[H-].[Na+]>CS(C)=O>[CH:1]1([O:6][C:7]2[C:14]([O:15][CH:16]([F:18])[F:17])=[CH:13][CH:12]=[CH:11][C:8]=2/[CH:9]=[CH:34]/[C:26]2[N:27]=[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]3[C:25]=2[C:23]([O:22][CH2:20][CH3:21])=[O:24])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 593698942-(Cyclopentyloxy)-3-(difluoromethoxy)benzaldehydeHCID 867617113-Ethyloxycarbonylimidazo[1,2-a]pyridine-2-yl-methyl(triphenyl)phosphonium bromide

Product 1

HCID 67548659Ethyl 2-{(E)-2-[2-(cyclopentyloxy)-3-(difluoromethoxy)phenyl]vinyl}imidazo [1,2-a]pyridine-3-carboxylateYield 76.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared by the reaction of 2-(cyclopentyloxy)-3-(difluoromethoxy)benzaldehyde (3.595 g, 14.040 mmol) with 3-ethyloxycarbonylimidazo[1,2-a]pyridine-2-yl-methyl(triphenyl)phosphonium bromide (7.0 g, 12.763 mmol) in the presence of NaH (0.561 g, 23.375 mmol) in anhydrous DMSO (15 mL) to afford 4.325 g of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.44 (t, J=6.9 Hz, 3H), 1.55-1.61 (m, 2H), 1.67-1.75 (m, 2H), 1.84-1.93 (m, 4H), 4.40-4.50 (m, 2H), 4.72-4.78 (m, 1H), 7.20 (t, J=74.7 Hz, 1H), 7.22-7.30 (m, 3H), 7.55-7.65 (m, 2H), 7.75 (d, J=8.7 Hz, 1H), 7.91 (d, J=16.8 Hz, 1H), 8.05 (d, J=16.2 Hz, 1H), 8.24 (d, J=5.1 Hz, 1H); APCI-MS (m/z) 443.28 (M)+.

Sources & evidence

ORD record
ord-b6042f806b1446eabc8d67d64663bdfd
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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