Potassium Carbonate → 1-(4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one

Reaction equation

[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[F:6][C:7]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([C:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=3)[S:18][C:11]=12.C([O-])([O-])=O.[K+].[K+]>>[F:6][C:7]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([C:19]3[CH2:20][CH2:21][N:22]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:23][CH:24]=3)[S:18][C:11]=12

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 13140Acryloyl chloride

HCID 59457731HCID 59457731, compound

Product 1

HCID 579196171-(4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)prop-2-en-1-oneYield 101.1%

Procedure

Acryloyl chloride (131.3 mL, 1.62 mmol) was added to a suspension of 7-(2-fluoro-4-nitrophenoxy)-2-(1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridine (85) [US 2007/0004675 A1] (150 mg, 0.40 mmol) and K2CO3 (223.4 1.62 mmol) and the mixture was stirred overnight at room temperature. It was then filtered and concentrated under reduced pressure affording title compound 98 (172 mg, 100% yield) that was used in the next step without further purification. MS (m/z): 426.1 (M+1)