Dichloromethane → (4-(1H-indol-5-yloxy)pyridin-2-yl)methanol

HRID 453232

反応式

HRID 453232 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:19][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 2763167(4-Chloropyridin-2-yl)methanol

生成物 1

HCID 59394421(4-(1H-indol-5-yloxy)pyridin-2-yl)methanol

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
160 °C

実験手順

To a solution of (4-chloropyridin-2-yl)methanol (384 mg, 2.67 mmol) in DMF (12 mL) is added 1H-indol-5-ol (534 mg, 4.01 mmol), and cesium carbonate (1307 mg, 4.01 mmol). The reaction is sealed and heated to 160° C. via microwave irradiation for 30 min. The reaction mixture is then cooled to room temperature and diluted brine and DCM. The resulting layers are separated and the aqueous layer is extracted three additional times with DCM. The organic layers are combined dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (0-100% EtOAc/heptane) to give the title compound. MS (ESI) m/z 241.2 (M+1).

後処理

  1. customThe reaction is sealed
  2. temperatureThe reaction mixture is then cooled to room temperature
  3. customThe resulting layers are separated
  4. extractionthe aqueous layer is extracted three additional times with DCM
  5. dry with materialThe organic layers are combined dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified via FCC (0-100% EtOAc/heptane)

出典と根拠

ORDレコード
ord-107983992ccc44b7848065f643ca1a1f
出典データセット
uspto-grants-2013_07
特許番号
US08492393B2

関連ノート

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