Potassium Carbonate → HCID 178436984, compound

HRID 1192526Notes

Reaction equation

HRID 1192526 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])/[N:4]=[N:5]/[C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:10]([C:19](=[O:21])[CH3:20])[CH:9]=[C:8]([F:22])[C:7]=1[C:23]#[C:24][Si](C)(C)C)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CO>[CH2:29]([N:3]([CH2:1][CH3:2])/[N:4]=[N:5]/[C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:10]([C:19](=[O:21])[CH3:20])[CH:9]=[C:8]([F:22])[C:7]=1[C:23]#[CH:24])[CH3:30]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178464416HCID 178464416, compound

Product 1

HCID 178436984HCID 178436984, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-{6-[(1E)-3,3-diethyltriaz-1-en-1-yl]-3′,4-difluoro-5-[(trimethylsilyl)ethynyl]biphenyl-2-yl}ethanone (2.0 g, 4.6 mmol) in tetrahydrofuran (39 mL) and methanol (7.7 mL) was treated with powdered potassium carbonate (3.2 g, 23 mmol) and stirred at 0° C. for 2 hours. The reaction mixture was filtered and the filtrate was treated with a few drops of water. The filtrate was concentrated to an oil that was diluted with ethyl acetate (150 mL), washed with water (50 mL) and brine (25 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (1.6 g, 99%) that was used without further purification. LCMS for C20H20F2N3O (M+H)+: m/z=356.2; Found: 355.9.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was treated with a few drops of water
  3. concentrationThe filtrate was concentrated to an oil that
  4. additionwas diluted with ethyl acetate (150 mL)
  5. washwashed with water (50 mL) and brine (25 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e3bf351308ba46d38403f7ebab394107
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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