Water → {2-[1-acetyl-3-(2,5-difluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-5-yl]ethyl}(dimethyl)silanol

HRID 1864760Notes

Reaction equation

HRID 1864760 reaction equation
[C:1]([N:4]1[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH:9]=[CH2:10])[CH2:7][C:6]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[N:5]1)(=[O:3])[CH3:2].Cl[SiH:26]([CH3:28])[CH3:27].O.CC[O:32]C(C)=O>C1(C)C=CC=CC=1.O.Cl.Cl.Cl[Pt](Cl)(Cl)Cl>[C:1]([N:4]1[C:8]([CH2:9][CH2:10][Si:26]([CH3:28])([CH3:27])[OH:32])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][C:6]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[N:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 66108ChlorodimethylsilaneHCID 579754961-Acetyl-3-(2,5-difluorophenyl)-5-phenyl-5-vinyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 11675753{2-[1-acetyl-3-(2,5-difluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-5-yl]ethyl}(dimethyl)silanol

Reagents, catalysts & solvents 2

HCID 16211507Platinate(2-), hexachloro-, hydrogen, hydrate (1:2:1), (OC-6-11)-CatalystHCID 1140TolueneSolvent

Procedure

To a solution of 100 mg (0.31 mmol) of 1-4 in 1 mL of toluene was added 51 μL (0.46 mmol) of chlorodimethylsilane and 13 mg (0.03 mmol) of hydrogen hexachloroplatinate(IV) hydrate. The reaction mixture was heated at 85° C. for 18 hours in a sealed tube before 500 μL of water was added. Heating was continued for 15 minutes then the reaction was cooled to room temperature, dumped into a separatory funnel containing EtOAc, washed successively with water, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with EtOAc/hexanes to provide 1-5 as a white solid. Data for 1-5: 1HNMR (500 MHz, CDCl3) δ 7.65 (m, 1H), 7.25 (m, 5H), 7.0 (m, 2H), 3.6-3.3 (m, 2H), 2.9 (m, 1H), 2.4 (m, 3H), 2.15 (m, 1H), 0.6-0.3 (m, 2H), 0.15 (m, 6H) ppm. HRMS (MALDI) calc'd M+H for C21H24F2N2O2Si: 403.1648 Found: 403.1637.

Workup

  1. additionwas added
  2. temperatureHeating
  3. customdumped into a separatory funnel
  4. washwashed successively with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography with EtOAc/hexanes

Sources & evidence

ORD record
ord-4dd5937618694156bb9cddf553b85a33
Source dataset
uspto-grants-2009_12
Patent number
US07625936B2

Reaction notes

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