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

HRID 338234노트

반응식

HRID 338234 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-f87324e8a05b4325b2b6cb578d757ebb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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