Hydrochloric Acid → 6-Chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol

HRID 1776849ノート

反応式

HRID 1776849 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.Cl.[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

5

反応物 3

HCID 313Hydrochloric AcidHCID 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/con. HCl (60 mL/40 mL) was stirred under reflux for 3 hours. The mixture was cooled to room temperature and adjusted to pH=7 by saturated NaOH and filtered though a Celit pad. The filtrate was extracted with EtOAc, washed by brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using silica gel chromatography (petroleum ether: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 hours
  2. filtrationfiltered though a Celit pad
  3. extractionThe filtrate was extracted with EtOAc
  4. washwashed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified

出典と根拠

ORDレコード
ord-807e9b9902d647359d27e99619788d9a
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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