1,1,1-Trifluoro-2,4-pentanedione → 2,2,2-trifluoro-1-[4-(4-methoxy-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone

HRID 133501

반응식

HRID 133501 반응식
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=O.[F:20][C:21]([F:29])([F:28])[C:22](=[O:27])[CH2:23][C:24](=O)[CH3:25]>C(O)(=O)C.S(=O)(=O)(O)O>[F:20][C:21]([F:29])([F:28])[C:22]([C:23]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:3]2[C:4]3[CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]2=[N:1][C:24]=1[CH3:25])=[O:27]

참가 물질

5

반응물 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 283374403-(4-methoxybenzoyl)-4H,5H,6H-cyclopenta[b]thiophen-2-amine

생성물 1

HCID 115456062,2,2-trifluoro-1-[4-(4-methoxy-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone수율 28.4%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 50 mg (0.18 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone in 2 ml acetic acid was added 0.022 ml (0.18 mmol) of 1,1,1-trifluoro-pentane-2,4-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 9:1) afforded 20 mg (28%) 2,2,2-trifluoro-1-[4-(4-methoxy-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a white solid. ES-MS m/e (%): 392 (M+H+, 100).

후처리

  1. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-38317f5fcbc64e05a0bb1813b07518c1
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390903B2

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