Potassium Carbonate → 3-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

HRID 1253469노트

반응식

HRID 1253469 반응식
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]#[C:19][Si](C)(C)C)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CO.C(OCC)(=O)C>[C:18]([C:17]1[CH:16]=[N:15][N:5]2[CH:6]=[C:7]([C:9]3[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=3)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=12)#[CH:19]

참가 물질

6

반응물 2

HCID 11430Potassium CarbonateHCID 584048004-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-[(trimethylsilyl)ethynyl]pyrazolo[1,5-a]pyridine

생성물 1

HCID 584046903-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a 0.10 M solution of 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-[(trimethylsilyl)ethynyl]pyrazolo[1,5-a]pyridine (788 mg, 2.43 mmol) in tetrahydrofuran and methanol (1:1, v/v) was added potassium carbonate (336 mg, 2.43 mmol). The reaction mixture was stirred at ambient temperature for two hours, and then diluted with ethyl acetate. The mixture was washed with saturated aqueous ammonium chloride and brine. The organic layer was separated, and the aqueous layer was back extracted with ethyl acetate three times. The combined organic layers was dried over sodium sulfate, filtered and concentrated to give 3-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine. LRMS (ESI) calculated for C14H13N4O [M+H]+, 252.1; found 253.0.

후처리

  1. washThe mixture was washed with saturated aqueous ammonium chloride and brine
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back extracted with ethyl acetate three times
  4. dry with materialThe combined organic layers was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6a802ff67dfa4327adc94bf2d01fd457
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

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