Water → 3-[(4-Fluoro-2-methylphenyl)(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561584

反応式

HRID 561584 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)O)=[C:4]([CH3:17])[CH:3]=1.[Cl-].[In+3].[Cl-].[Cl-].ClC1C=C(Cl)C=CC=1C([C:34]1[C:42]2[C:37](=[C:38]([CH2:44][S:45][CH3:46])[CH:39]=[C:40](F)[CH:41]=2)[NH:36][CH:35]=1)CCO.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:34]2[C:42]3[C:37](=[C:38]([CH2:44][S:45][CH3:46])[CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)=[C:4]([CH3:17])[CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 159675indium(III)chlorideHCID 58392149HCID 58392149、化合物HCID 583923053-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

生成物 1

HCID 445952363-[(4-Fluoro-2-methylphenyl)(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

509 mg (2.17 mmol) of the compound from Example 82A and 437 mg (1.97 mmol) of indium(III) chloride were added to 350 mg (1.97 mmol) of the compound from Example 8 in 15 ml of toluene. The reaction mixture was stirred at 80° C. for 5 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate, and the solid was filtered off. The phases of the filtrate were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 174 mg (22% of theory) of the title compound.

後処理

  1. temperatureAfter cooling to RT
  2. filtrationthe solid was filtered off
  3. customThe phases of the filtrate were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

出典と根拠

ORDレコード
ord-582347a2ca0841c687b16d7d189cb27a
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

関連ノート

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