Water → HCID 68689628, compound

HRID 1296276Notes

Reaction equation

HRID 1296276 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:34][CH2:33][N:11]2[C:12](=[O:32])[C:13]3[C:18]([CH:10]2[CH2:9]1)=[CH:17][C:16](OS(C(F)(F)F)(=O)=O)=[CH:15][C:14]=3[O:27][C:28]([F:31])([F:30])[F:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:35]1(B2OC(C)(C)C(C)(C)O2)[CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC>[C:1]([O:5][C:6]([N:8]1[CH2:34][CH2:33][N:11]2[C:12](=[O:32])[C:13]3[C:18]([CH:10]2[CH2:9]1)=[CH:17][C:16]([CH:35]1[CH2:37][CH2:36]1)=[CH:15][C:14]=3[O:27][C:28]([F:29])([F:30])[F:31])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86614990HCID 86614990, compound

Product 1

HCID 68689628HCID 68689628, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirring degassed solution of N-(t-butoxycarbonyl)-(±)-1,3,4,10b-tetrahydro-9-trifluormethylsulfonyloxy-7-trifluoromethoxy-pyrazino[2,1-a]isoindol-6(2H)-one (100 mg, 0.19 mmol), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (101 mg, 0.6 mmol), and potassium carbonate (138 mg, 1.0 mmol) in DME (2 mL) under Ar was added bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex (5 mg, 0.006 mmol) and water (0.2 mL). The reaction was heated to reflux for 3 h and then cooled to room temperature. The reaction was quenched with 1M NaOH and extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc in vacuo to a brown oil. The oil was purified by flash chromatography (SiO2, 0–50% EtOAc in hexanes) to yield 70 mg of the desired product as a white solid. MS (ESI) 413 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 h
  3. customThe reaction was quenched with 1M NaOH
  4. extractionextracted with EtOAc (3×5 mL)
  5. dry with materialdried over Na2SO4
  6. customThe oil was purified by flash chromatography (SiO2, 0–50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fe1edf91bc7546df92741a480e187d05
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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