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

HRID 1054786ノート

反応式

HRID 1054786 の反応式
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=3[Cl:20])[NH:16][CH:15]=[C:14]4[CH:21]=[O:22])=[CH:7][CH:6]=2)[CH2:2]1.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(=CC)C.CC(O)(C)C.O>[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=3[Cl:20])[NH:16][CH:15]=[C:14]4[C:21]([OH:24])=[O:22])=[CH:7][CH:6]=2)[CH2:2]1

参加物

6

反応物 4

HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866987735-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde

生成物 1

HCID 866987745-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acid収率 10.2%

試薬・触媒・溶媒 1

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

実験手順

To 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (94 mg, 0.30 mmol) in 2-methyl-2-butene/t-BuOH/H2O (v/v/v=1/1/1, 4 mL) was added sodium dihydrogen phosphate (364 mg, 3.04 mmol) and sodium chlorite (274 mg, 3.04 mmol) at room temperature. The resulting mixture was stirred at room temperature for 24 hours. To the reaction mixture was added sodium sulfite (383 mg, 3.04 mmol), then concentrated in vacuo and purified via reverse phase HPLC to give the title compound (10 mg, 10% yield). 1H NMR (400 MHz, CD3OD) δ 8.03-80.4 (d, 2 H), 7.62 (s, 1 H), 7.48-7.52 (m, 4 H), 4.44-4.48 (m, 2 H), 4.32-4.34 (m, 3 H).

後処理

  1. concentrationconcentrated in vacuo
  2. custompurified via reverse phase HPLC

出典と根拠

ORDレコード
ord-4acf7e2388934e91ba3ebdd460d31c8d
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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