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

HRID 595555ノート

反応式

HRID 595555 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-da1c0866e72143b5bd026a8a81a9bf34
出典データセット
uspto-grants-2016_01
特許番号
US09242998B2

反応ノート

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