Sodium Sulfite → 6-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carboxylic acid

HRID 1054760

反応式

HRID 1054760 の反応式
[Cl: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][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(=CC)C.C(O)(C)(C)C.O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:24])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987526-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carbaldehyde

生成物 1

HCID 866987536-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carboxylic acid収率 14%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 230840282-Methyl-2-butene t-butanol water溶媒

実験手順

To 6-chloro-5-[4-(3-hydroxypropyl)phenyl]-1H-indole-3-carbaldehyde (40 mg, 0.13 mmol) in 2-methyl-2-butene/t-butanol/water (v/v/v=1/1/1, 6 mL) was added sodium dihydrogen phosphate (30.5 mg, 0.254 mmol) and sodium chlorite (23 mg, 0.25 mmol) at room temperature. The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was added sodium sulfite (0.254 mmol), diluted with water, extracted with EtOAc, then concentrated in vacuo and purified via preparative HPLC to give the title compound (6.0 mg, 14% yield).

後処理

  1. extractionextracted with EtOAc
  2. concentrationconcentrated in vacuo
  3. custompurified via preparative HPLC

出典と根拠

ORDレコード
ord-57ca515a1c2d4a23a14ae3dff608bb0f
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

関連ノート

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