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

HRID 1253469Notes

Reaction equation

HRID 1253469 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6a802ff67dfa4327adc94bf2d01fd457
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

Loading…