Sodium Hydroxide → 6-Chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol

HRID 595555노트

반응식

HRID 595555 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[C:5]([OH:18])=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[F:17])[NH:9]2)[C:5]([OH:18])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 867262926-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol

생성물 1

HCID 867262936-Chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol수율 80%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol (10 g, 38 mmol) and metal Sn (23 g, 190 mmol) in CH3CH2OH/concentrated HCl (60 mL/40 mL) was stirred under reflux for 3 h. The mixture was cooled to room temperature and adjusted to pH=7 by saturated NaOH and filtered though a Celite pad. The filtrate was extracted with EtOAc, washed by brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=10:1) to get 6-chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol (8 g, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 9.86 (s, 1H), 7.10˜7.20 (m, 3H), 6.33˜6.91 (m, 2H), 5.15˜5.21 (m, 1H), 4.61 (s, 1H), 3.65˜3.71 (m, 1H), 3.04˜3.11 (m, 1H). MS (M+H)+: 265.

후처리

  1. temperatureunder reflux for 3 h
  2. filtrationfiltered though a Celite pad
  3. extractionThe filtrate was extracted with EtOAc
  4. washwashed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (PE:EtOAc=10:1)

출처 및 근거

ORD 기록
ord-da1c0866e72143b5bd026a8a81a9bf34
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242998B2

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