2-Methyl-2-butene → 6-fluoro-5-[4-(hydroxymethyl)phenyl]-1H-indole-3-carboxylic acid

HRID 1054577노트

반응식

HRID 1054577 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=1.CC(=CC)C.Cl([O-])=[O:27].[Na+].O.P([O-])(O)(O)=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:27])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=1

참가 물질

8

반응물 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 866985806-fluoro-5-[4-(hydroxymethyl)phenyl]-1H-indole-3-carbaldehyde

생성물 1

HCID 866985816-fluoro-5-[4-(hydroxymethyl)phenyl]-1H-indole-3-carboxylic acid수율 29.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6386tert-Butanol용매

반응 조건

온도
0 °C

실험 절차

A solution of 6-fluoro-5-[4-(hydroxymethyl)phenyl]-1H-indole-3-carbaldehyde (65 mg, 0.24 mmol) in acetonitrile (3 mL) and tert-butanol (3 mL) was treated with 2-methyl-2-butene (2 mL, 18.4 mmol) and cooled to 0° C. A solution of sodium chlorite (410 mg, 4.9 mmol) and sodium dihydrogen phosphate monohydrate (684 mg, 4.96 mmol) in water (3 mL) was added dropwise via an addition funnel. The reaction mixture was warmed to room temperature and stirred for 65 hours. The reaction was partially evaporated in vacuo, and partitioned between water and ethyl acetate. The organic phase was concentrated in vacuo. The crude material was purified using reverse-phase chromatography to give the title compound (20.4 mg).

후처리

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customThe reaction was partially evaporated in vacuo
  3. custompartitioned between water and ethyl acetate
  4. concentrationThe organic phase was concentrated in vacuo
  5. customThe crude material was purified

출처 및 근거

ORD 기록
ord-33b50446266147c68623b7401ae320e4
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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