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

HRID 1942781Notes

Reaction equation

HRID 1942781 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

4

Reactant 3

HCID 11430Potassium CarbonateHCID 13140Acryloyl chlorideHCID 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)

Workup

  1. filtrationIt was then filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-621e9026be774efe8f24ebd9bffb7394
Source dataset
uspto-grants-2013_03
Patent number
US08389541B2

Reaction notes

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