Potassium Carbonate → HCID 178437994, 화합물

HRID 1520020노트

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HRID 1520020 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 178437994HCID 178437994, 화합물수율 95.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b15e35665bd7400c91a3772a6a740413
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073892B2

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