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

HRID 1634072ノート

反応式

HRID 1634072 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A yellow suspension of 6-(bromomethyl)-1H-indazole hydrogen bromide (9.0 g, 43 mmol) (5) and 3,4-dihydro-2H-pyran (7.2 g, 86 mmol) in THF (200 mL) was heated at reflux for 2 hours. The reaction mixture was additionally 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) δ 1.57-1.84 (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).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was removed under vacuum
  6. customto give a yellow oil

出典と根拠

ORDレコード
ord-48430ce134a348cfbd1ef2461947f27d
出典データセット
uspto-grants-2003_01
特許番号
US06506754B1

反応ノート

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