Cesium carbonate → HCID 58007509, compound

HRID 1094383Notes

Reaction equation

HRID 1094383 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CC(OC)(C)C>[CH3:1][N:2]1[C:6]([N:7]([CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:36][CH:37]=2)[C:8](=[O:17])[C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][C:4]([CH3:18])=[N:3]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 149499411-(2-Bromoethyl)-4-(trifluoromethyl)benzene2×HCID 58007534HCID 58007534, compound

Product 1

HCID 58007509HCID 58007509, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of N-(2,5-dimethyl-2H-pyrazol-3-yl)-2-oxo-2-phenyl-acetamide (200 mg, 0.82 mmol) in DMF (2 mL) was added at 0° C. potassium bis(trimethylsilyl)amide (0.91 M in THF, 1.1 mL, 0.99 mmol) over a period of 5 min. The ice bath was removed and the solution was stirred for 1 h at ambient temperature. After the addition of 1-(2-bromo-ethyl)-4-trifluoromethyl-benzene (which might be prepared according to WO2005123748, 250 mg, 0.99 mmol) the reaction mixture was stirred for 18 h at ambient temperature. After the addition of cesium carbonate (1.40 g, 4.11 mmol) and further 1-(2-bromo-ethyl)-4-trifluoromethyl-benzene (996 mg, 3.95 mmol) it was stirred for 20 h at ambient temperature. The resulting mixture was diluted with TBME (15 mL) and washed twice with water (10 mL) and brine (10 mL). The combined aqueous layers were extracted with TBME (15 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (113 mg, 33%) as a light brown oil. MS m/e: 416.3 [M+H]+.

Workup

  1. customThe ice bath was removed
  2. stirringwas stirred for 18 h at ambient temperature
  3. stirringwas stirred for 20 h at ambient temperature
  4. washwashed twice with water (10 mL) and brine (10 mL)
  5. extractionThe combined aqueous layers were extracted with TBME (15 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record
ord-c8f476fd74ca4195af549c10a2335ded
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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