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

HRID 450319

반응식

HRID 450319 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
160 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-047362d79109474b93c5a709430068f9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486954B2

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