3,4-dihydro-2H-pyran → 6-(Bromomethyl)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazole

HRID 1263439노트

반응식

HRID 1263439 반응식
Br.[Br:2][CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C1COCC1.C(Cl)Cl>[Br:2][CH2:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 513419766-(Bromomethyl)-1H-indazole hydrobromide

생성물 1

HCID 186161856-(Bromomethyl)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazole수율 72%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A yellow-suspension of 6-(bromomethyl)-1H-indazole hydrogen bromide (9.0 g, 43 mmol) (99) and 3,4-dihydro-2H-pyran (7.2 g, 86 mmol) in THF (200 mL) was heated at its reflux temperature for 2 hours. After cooling down to room temperature, the reaction mixture was stirred at room temperature for 12 hours under nitrogen. The reaction solution was diluted with methylene chloride (500 mL), washed with saturated NaHCO3, water and brine. After drying (MgSO4) the solvent was removed under vacuum to give a yellow oil. Flash chromatography yielded the title compound (6.6 g, 72%). TLC Rf 0.52 (80:20 of hexane-ethyl acetate); MS (electrospray) 295, 297 (M+1); 1H N MR: (CDCl3) δ1.57-1.84 (m, 3H), 2.16 (m, 2H), 2.55 (m, 1H), 3.75 (m, 1H), 4.01 (m, 1H), 4.65 (s, 2H), 5.71 (d, 1H, J=9.2 Hz), 7.44 (d, 1H, J=8.8 Hz), 7.59 (d, 1H, J=8.8 Hz), 7.73 (s, 1H), 8.00 (s, 1H).

후처리

  1. temperaturewas heated at its
  2. temperaturereflux temperature for 2 hours
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialAfter drying (MgSO4) the solvent
  5. customwas removed under vacuum
  6. customto give a yellow oil

출처 및 근거

ORD 기록
ord-def27c6950214049823e76ac5b850171
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541467B1

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