2-Methyl-2-butene → 5-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carboxylic acid

HRID 338249

反応式

HRID 338249 の反応式
[N:1]1([C:5](=[O:25])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][C:21]=3[Cl:22])[NH:18][CH:17]=[C:16]4[CH:23]=[O:24])=[CH:9][CH:8]=2)[CH2:4][CH2:3][CH2:2]1.CC(=CC)C.Cl([O-])=[O:32].[Na+].O.O.OP([O-])(O)=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[N:1]1([C:5](=[O:25])[CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][C:21]=3[Cl:22])[NH:18][CH:17]=[C:16]4[C:23]([OH:32])=[O:24])=[CH:9][CH:8]=2)[CH2:4][CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 105532-Methyl-2-butene2 回HCID 23668197Sodium Chlorite2 回HCID 23673460Sodium Phosphate, Monobasic, Dihydrate2 回HCID 866985935-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carbaldehyde

生成物 1

HCID 866985945-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carboxylic acid収率 15%

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

To a solution of 5-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carbaldehyde (0.16 g, 0.453 mmol) in acetonitrile (8 mL) and tert-butanol (8 mL) was added 2-methyl-2-butene (8 mL). The reaction mixture was cooled to 0° C. and treated with a solution of sodium chlorite (456 mg, 5 mmol) and sodium phosphate monobasic dihydrate (1.06 g, 6.8 mmol) in water (6 mL). The reaction mixture was stirred for 2 hours at room temperature, and treated with additional sodium chlorite (607 mg, 6.67 mmol), sodium phosphate monobasic dihydrate (1.41 g, 9.04 mmol) and 2-methyl-2-butene (1 mL). The resulting mixture was stirred at room temperature overnight. The reaction mixture was partially evaporated in vacuo and extracted with EtOAc (30 mL×3). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified via prep-HPLC to give 5-{4-[2-(azetidin-1-yl)-2-oxoethyl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (25 mg) as a yellow solid.

後処理

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe reaction mixture was partially evaporated in vacuo
  3. extractionextracted with EtOAc (30 mL×3)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via prep-HPLC

出典と根拠

ORDレコード
ord-67e62c9af10a469380ac3869fff7a099
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

関連ノート

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