Potassium Carbonate → HCID 86055589, compound

HRID 2104794Notes

Reaction equation

HRID 2104794 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][Si](C)(C)C)[CH:19]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:30]([F:33])([F:32])[F:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:30]([F:33])([F:32])[F:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 669138383-Benzyl-8-trifluoromethyl-4-(3-trimethylsilanylethynylphenyl)-quinoline

Product 1

HCID 86055589HCID 86055589, compoundYield 140.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the above oil, 3-benzyl-8-trifluoromethyl-4-(3-trimethylsilanylethynylphenyl)-quinoline (730 mg, 1.6 mmol) and potassium carbonate (220 mg, 1.6 mmol) in methanol (30 mL) is stirred at ambient temperature for 3 h. The reaction mixture is stripped to dryness and the residue taken up in ethyl acetate and washed with 30 mL (1N HCl). The organic layer is dried and concentrated in vacuo to provide after chromatography 870 mg (80%) of the title compound: MS (ESI) m/z 388.

Workup

  1. washwashed with 30 mL (1N HCl)
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19b545460ec14e2383612abb084db23c
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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