HCID 53694173, compound → HCID 19016558, compound

HRID 1728771Notes

Reaction equation

HRID 1728771 reaction equation
[C:1]([NH:4][CH:5]([C:16](=[O:33])[CH:17]=[CH:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2]>O1CCCC1.[Pd]>[C:1]([NH:4][CH:5]([C:16](=[O:33])[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:20]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 53694173HCID 53694173, compound

Product 1

HCID 19016558HCID 19016558, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Acetamido-1-(3-benzo[b]thienyl)-5-(3,5-bistrifluoromethylphenyl)-4-penten-3-one (2.0 g) was hydrogenated in tetrahydrofuran (100 ml) using 10% Pd/C (0.5 g) at 50 p.s.i. The product was purified by chromatography on silica using ethyl acetate/petroleum ether (bp 60°-80° C.)(1:1) to yield the title compound as a white solid (1.2 g), mp=83°-84° C.; found: C, 56.41; H, 3.81; N, 2.84; C23H19F6NO2S requires C, 56.67; H, 3.93; N, 2.87%.

Workup

  1. customThe product was purified by chromatography on silica

Sources & evidence

ORD record
ord-321c03cb856c436c905dc7deb2364be4
Source dataset
uspto-grants-1994_07
Patent number
US05328927

Reaction notes

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