Potassium Carbonate → HCID 178437996, compound

HRID 1520002Notes

Reaction equation

HRID 1520002 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15](C(OC(C)(C)C)=O)[N:14]=1)(C)C>CCO>[C:12]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][N:14]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67981125tert-butyl 3-((trimethylsilyl)ethynyl)-1H-indazole-1-carboxylate

Product 1

HCID 178437996HCID 178437996, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium carbonate (880 mg, 6.4 mmol, 0.1 eq.) was added into a solution of tert-butyl 3-[(trimethylsilyl)ethynyl]-1H-indazole-1-carboxylate (20 g; 63.6 mmol; 1.0 eq.) in EtOH (400 mL) and the reaction mixture was stirred overnight at RT. Solvent was removed under vacuum while maintaining bath temperature below 25° C. The residue was dissolved in Et2O, washed with water (twice) and brine (four times). Organic layer was dried over magnesium sulfate, filtered and concentrated to afford the title compound as a brown solid (7.1 g, 80%). 1H NMR (300 MHz, DMSO-d6) δ: 13.44 (s, 1H), 7.71 (d, J=8.5 Hz, 1H), 7.59 (d; J=8.5 Hz, 1H), 7.41 (m, 1H), 7.22 (m, 1H), 4.50 (s, 1H).

Workup

  1. customSolvent was removed under vacuum
  2. temperaturewhile maintaining bath temperature below 25° C
  3. dissolutionThe residue was dissolved in Et2O
  4. washwashed with water (twice) and brine (four times)
  5. dry with materialOrganic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-658d6232161e46f58249e9490b24fa8c
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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