Tetrahydrofuran → HCID 68691525, compound

HRID 1296262Notes

Reaction equation

HRID 1296262 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16](Br)=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27](=O)([O-])[O-].[K+].[K+].[CH2:33]1[CH2:37]O[CH2:35][CH2:34]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH:33]([CH2:37][CH3:27])[CH2:34][CH3:35])=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 16115648HCID 16115648, compound

Product 1

HCID 68691525HCID 68691525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring degassed solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-bromo-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (66 mg, 0.15 mmol) and potassium carbonate (105 mg, 0.76 mmol) in DMF (1.0 mL) was added 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex (12 mg, 0.015 mmol). After 15 min., 0.5 M THF solution of 3-propenylzinc bromide (0.45 mL, 0.9 mmol) was added. The reaction was heated to reflux for 15 min and then cooled to room temp. The reaction was quenched with 1M aq. NaOH and extracted with EtOAc (3×10 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a black oil. The oil was purified by flash chromatography (silica gel, 0–50% EtOAc in hexanes) to give 36 mg of the desired product as a colorless oil. MS (ESI) 427 (M+H).

Workup

  1. additionwas added 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex (12 mg, 0.015 mmol)
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 15 min
  4. customThe reaction was quenched with 1M aq. NaOH
  5. extractionextracted with EtOAc (3×10 mL)
  6. dry with materialdried over Na2SO4
  7. customThe oil was purified by flash chromatography (silica gel, 0–50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e7d06e79765f4dd386481d27c4751e0b
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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