Potassium Carbonate → HCID 178437994、化合物

HRID 1520020ノート

反応式

HRID 1520020 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19](C(OC(C)(C)C)=O)[N:18]=[C:17]3[C:30]#[C:31][Si](C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CCO>[C:30]([C:17]1[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)[CH:15]=2)[NH:19][N:18]=1)#[CH:31]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 67981297tert-butyl 5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-3-[(trimethylsilyl)ethynyl]-1H-indazole-1-carboxylate

生成物 1

HCID 178437994HCID 178437994、化合物収率 95.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of tert-butyl 5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-3-[(trimethylsilyl)ethynyl]-1H-indazole-1-carboxylate (189 mg; 0.38 mmol; 1.0 eq.) and potassium carbonate (5.3 mg; 0.04 mmol; 0.1 eq.) in EtOH (3.8 mL) was stirred at RT O/N. EtOH was removed under reduced pressure and the residue was diluted with ether, washed with water then brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 60:40) to give the title compound as a beige solid (118 mg, 95%). 1H NMR (300 MHz, DMSO-d6) δ 13.35 (brs, 1H), 7.55-7.47 (m, 2H), 7.33 (dd, J=1.6, 8.6 Hz, 1H), 4.48 (s, 1H), 4.15-4.03 (m, 2H), 2.93-2.71 (m, 3H), 1.86-1.74 (m, 2H), 1.65-1.45 (m, 2H), 1.42 (s, 9H). HPLC (Condition A): Rt 4.78 min (purity 99.1%).

後処理

  1. customEtOH was removed under reduced pressure
  2. additionthe residue was diluted with ether
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 60:40)

出典と根拠

ORDレコード
ord-b15e35665bd7400c91a3772a6a740413
出典データセット
uspto-grants-2015_07
特許番号
US09073892B2

反応ノート

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