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

HRID 561601
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HRID 561601 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:19]1[C:27]2[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[CH2:13][C:14](OCC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:19]1[C:27]2[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[CH2:13][CH2:14][OH:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392306Ethyl 3-[2-chloro-4-(trifluoromethyl)phenyl]-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

생성물 1

HCID 583922483-[2-Chloro-4-(trifluoromethyl)phenyl]-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
3회

실험 절차

A solution of 1.30 g (2.85 mmol) of the compound from Example 99A in 20 ml of THF was added dropwise to 10 ml (9.98 mmol) of a 1N lithium aluminum hydride solution in THF under argon in 80 ml of THF at RT. 1N hydrochloric acid was then added, the mixture was extracted with dichloromethane, 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 0.73 g (61% of theory) of the title compound.

후처리

  1. extractionthe mixture was extracted with dichloromethane
  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-3a3bc7ea155a48c69eed851731d066b7
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063234B2

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