Water → 3-(4-Chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561527노트

반응식

HRID 561527 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(#N)C.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:25][S:26][CH3:27])[C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6342AcetonitrileHCID 21226445Aluminium lithium hydrideHCID 58392255Ethyl 3-(4-chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

생성물 1

HCID 583923413-(4-Chlorophenyl)-3-{6-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
60 °C

실험 절차

A solution of 2.33 g (5.7 mmol) of the compound from Example 47A in 18 ml of tetrahydrofuran was added dropwise to 20.1 ml (60.1 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran and 20 ml of tetrahydrofuran at RT. The mixture was stirred at 60° C. for 1 h, acetonitrile was added, and water was added to the solution while cooling in ice. The solid was filtered off with suction from the suspension, the filtrate was concentrated, and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.72 g (82% of theory) of the title compound were obtained.

후처리

  1. temperaturewhile cooling in ice
  2. filtrationThe solid was filtered off with suction from the suspension
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-1994f88aa1fd4d3287a15a240387ad6f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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