Water → 3-{5-Amino-3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-pyrazol-1-yl}-phenol

HRID 630972ノート

反応式

HRID 630972 の反応式
C([O:8][C:9]1[CH:10]=[C:11]([N:15]2[C:19]([NH2:20])=[CH:18][C:17]([C:21]([CH3:42])([CH3:41])[CH2:22][O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:16]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:20][C:19]1[N:15]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[N:16]=[C:17]([C:21]([CH3:42])([CH3:41])[CH2:22][O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:18]=1

参加物

6

反応物 3

HCID 962WaterHCID 2723923Ammonium formateHCID 866872842-(3-Benzyloxy-phenyl)-5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-2H-pyrazol-3-ylamine

生成物 1

HCID 866872853-{5-Amino-3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-pyrazol-1-yl}-phenol収率 52%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of Intermediate 153c (1.21 g, 2.1 mmol) in ethanol (IMS grade, 20 mL) was treated with water (1 mL) and ammonium formate (1.33 g, 21 mmol). The mixture was purged with N2 then 10% Pd/C (0.67 g, 0.63 mmol Pd) was added. The mixture was heated to reflux for 1 h then filtered through celite and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and water. The phases were separated and the aqueous layer was extracted with EtOAc (×2). The combined organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by FCC, using 0-40% EtOAc in cyclohexane, to give the title compound (0.53 g, 41% over 2 steps) as a golden gum. LCMS (Method 3): Rt 4.55 min, m/z 486.5 [MH+].

後処理

  1. customThe mixture was purged with N2
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 h
  4. filtrationthen filtered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between EtOAc and water
  7. customThe phases were separated
  8. extractionthe aqueous layer was extracted with EtOAc (×2)
  9. washThe combined organic phase was washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-09d3bfd3fa07401a9e1a92910fbef5b5
出典データセット
uspto-grants-2016_04
特許番号
US09315503B2

反応ノート

読み込み中…