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

HRID 338417

반응식

HRID 338417 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 230840282-Methyl-2-butene t-butanol water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d57b8685538e46dcb79054233b08a41f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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