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

HRID 1054786노트

반응식

HRID 1054786 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 230840282-Methyl-2-butene t-butanol water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4acf7e2388934e91ba3ebdd460d31c8d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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