Sodium Carbonate → HCID 53495831, compound

HRID 1868150Notes

Reaction equation

HRID 1868150 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:32])[CH2:9]2)=[C:4]([C:33]([F:36])([F:35])[F:34])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:63]([C:65]([F:68])([F:67])[F:66])=[CH2:64]>C1COCC1.CCOCC.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:63]([C:65]([F:68])([F:67])[F:66])=[CH2:64])[CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:32])[CH2:9]2)=[C:4]([C:33]([F:34])([F:36])[F:35])[CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 53495830HCID 53495830, compound

Product 1

HCID 53495831HCID 53495831, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylsulfonyl)piperazine (106 mg, 0.2 mmol) and Pd(PPh3 (12 mg, 0.01 mmol) in THF (2 mL) was degassed and then added Na2CO3 (0.6 mL, 1.0 M in water, 0.6 mmol) and 2-bromo-3,3,3-trifluoroprop-1-ene (105 mg, 0.6 mmol) under N2. The resultant mixture was heated in a sealed tube in an oil bath at 60° C. overnight. After cooling, diluted with Et2O (10 mL), washed with brine and extracted with Et2O. The combined organic layer was dried over Na2SO4. The crude product was purified on SiO2 gel column eluted with hexanes/EtOAc to give (R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methyl-1-(3-(3,3,3-trifluoroprop-1-en-2-yl)phenylsulfonyl)piperazine as a colorless oil (83 mg, 85%).

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. customThe crude product was purified on SiO2 gel column
  6. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-f64c5b39a0244d4984eee5ad0ecf10d8
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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