1-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone → 1-(2-Methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-ethanone

HRID 133524

反応式

HRID 133524 の反応式
[CH3:1][C:2]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1>C1(C=CC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][C:2]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11]3[C:6](=[CH:7][N:8]=[CH:9][CH:10]=3)[S:5][C:4]=2[N:3]=1

参加物

4

反応物 1

HCID 688965541-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone

生成物 1

HCID 115514681-(2-Methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-ethanone収率 11%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 11502Stilbene溶媒

反応条件

温度
150 °C

実験手順

To a stirred solution of 0.70 g (2.17 mmol) 1-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone in 10 ml diphenylethylene was added 325 mg palladium on charcoal 10%. The mixture was stirred over night at 150° C., and then poured onto ethyl acetate (about 150 ml), and extracted three times aqueous HCl (1M). The combined aqueous phases were basified with K2CO3 until ph=8, and then the product was extracted with ethyl acetate. The combined organic phase were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 75 mg (11%) 1-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-ethanone as a light yellow solid. ES-MS m/e (%): 319 (M+H+, 100).

後処理

  1. additionpoured onto ethyl acetate (about 150 ml)
  2. extractionextracted three times aqueous HCl (1M)
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe combined organic phase were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-14452336198b4e7584a35ac75d147b6a
出典データセット
uspto-grants-2008_06
特許番号
US07390903B2

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