Water → 6-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole

HRID 1634152노트

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HRID 1634152 반응식
Br[CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1)=[N+:19]=[N-:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 186161856-(Bromomethyl)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazole

생성물 1

HCID 186161896-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of 6-(bromomethyl)-1-(2-tetrahydropyranyl)indazole (4.0 g, 14 mmol) (6) in DMF (30 mL) was added sodium azide (6 g, 92 mmol) in one portion. The suspension was heated at 90° C. for 30 minutes and a yellow solution was formed. After cooling down to room temperature, the reaction mixture was poured into water (100 mL) and extracted with ether (2×150 mL). Combined organic layers were washed with brine then dried (MgSO4). Evaporation of solvent gave an yellow oil which was purified by column chromatography to yield title compound (2.91 g, 83%). TLC Rf 0.31 (70:30 of hexane-ethyl acetate); MS (electrospray) 258 (M+1); 1H NMR (CDCl3) δ 1.75 (m, 3H), 2.10 (m, 2H), 2.55 (m, 1H), 3.72 (m, 1H), 4.01 (m, 1H), 4.48 (s, 2H), 5.73 (dd, 1H, J=8.2, 2.8 Hz), 7.12 (dd, 1H, J=8.2, 0.8 Hz), 7.55 (s, 1H), 7.71 (d, 1H, J=8.2 Hz), 8.02 (s, 1H).

후처리

  1. customa yellow solution was formed
  2. temperatureAfter cooling down to room temperature
  3. extractionextracted with ether (2×150 mL)
  4. washCombined organic layers were washed with brine
  5. dry with materialthen dried (MgSO4)
  6. customEvaporation of solvent
  7. customgave an yellow oil which
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-86955b48b9cb495cba9c8a58b2d79b68
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506760B1

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