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

HRID 133493

反応式

HRID 133493 の反応式
[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[S:13][CH:14]=[CH:15][CH:16]=1)=O.[F:17][C:18]([F:26])([F:25])[C:19](=[O:24])[CH2:20][C:21](=O)[CH3:22]>C(O)(=O)C.S(=O)(=O)(O)O>[F:17][C:18]([F:26])([F:25])[C:19]([C:20]1[C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[C:3]2[C:4]3[CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]2=[N:1][C:21]=1[CH3:22])=[O:24]

参加物

5

反応物 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 9899694(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone

生成物 1

HCID 115379172,2,2-trifluoro-1-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-ethanone収率 22%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 59 mg (0.24 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone in 2 ml acetic acid was added 0.038 ml (0.24 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 20:1) afforded 19 mg (22%) 2,2,2-trifluoro-1-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-ethanone as a colorless oil. ES-MS m/e (%): 368 (M+H+, 100).

後処理

  1. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2b7846bc67544912bcb39f7beac778dd
出典データセット
uspto-grants-2008_06
特許番号
US07390903B2

関連ノート

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