Sodium hydride → tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate

HRID 512862ノート

反応式

HRID 512862 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineHCID 178423506-Fluoro-1H-indazole

生成物 1

HCID 89614504tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 6-fluoro-1H-indazole (6.46 mmol, 880 mg) in DMF (15 mL) cooled to 0° C. under Ar was added 95% NaH (6.46 mmol, 163 mg). The resulting mixture was stirred for 15 minutes before tert-butyl 4-(tosyloxy)piperidine-1-carboxylate (7.11 mmol, 2.52 g) was added. After an additional 15 minutes at 0° C., the ice bath was removed and the reaction vessel placed in a 110° C. bath for 2.75 hours. After cooling to ambient temperature, the DMF was removed in vacuo and ethyl acetate (100 mL) was added. The organic layer was washed with water and brine, dried (MgSO4), filtered and the solvent removed in vacuo. The resulting residue was purified by SiO2 column chromatography (0-40% EtOAc/hexanes) to yield tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate.

後処理

  1. additionwas added
  2. customthe ice bath was removed
  3. customplaced in a 110° C.
  4. customfor 2.75 hours
  5. customthe DMF was removed in vacuo and ethyl acetate (100 mL)
  6. additionwas added
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customThe resulting residue was purified by SiO2 column chromatography (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ddaf614fcc5d4af485d6b4ee1e9fa421
出典データセット
uspto-grants-2015_08
特許番号
US09102669B2

反応ノート

読み込み中…