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Hydrochloric Acid → 3-(4-Chloro-2-methylphenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561600
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HRID 561600 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])[CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[C:4]([CH3:28])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[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])[CH:20]=[C:21]([F:24])[CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[C:4]([CH3:28])[CH:3]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392476Ethyl 3-(4-chloro-2-methylphenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

생성물 1

HCID 583921093-(4-Chloro-2-methylphenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매
3회

실험 절차

A solution of 690 mg (1.64 mmol) of the compound from Example 98A in 10 ml of THF was added dropwise to 5.8 ml (5.75 mmol) of a 1N lithium aluminum hydride solution in THF under argon in 20 ml of THF at RT. 1N hydrochloric acid was then added, the mixture was extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 0.60 g (97% of theory) of the title compound.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

출처 및 근거

ORD 기록
ord-d93bba2fa21345d3aed9d697a075e2d8
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063234B2

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