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

HRID 1054577ノート

反応式

HRID 1054577 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33b50446266147c68623b7401ae320e4
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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