Butyl vinyl ether → HCID 67491110, compound

HRID 571967Notes

Reaction equation

HRID 571967 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:12]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([N:22]3[CH:26]=[N:25][N:24]=[CH:23]3)[CH2:17]2)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH2:27]([O:31]C=C)[CH2:28]CC.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:27]([C:2]1[CH:3]=[C:4]([S:12]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([N:22]3[CH:26]=[N:25][N:24]=[CH:23]3)[CH2:17]2)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1)(=[O:31])[CH3:28]

Participants

6

Reactant 3

HCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 49869093HCID 49869093, compound

Product 1

HCID 67491110HCID 67491110, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Palladium acetate (9.9 mg, 0.044 mmol) was added to a stirred solution of 3a (100 mg, 0.221 mmol), n-butylvinyl ether (221 mg, 2.206 mmol) and triethylamine (92.0 μL, 0.662 mmol) in DMF (2.00 mL), and the resulting mixture was degassed and heated to 80° C. After 6 h, the reaction mixture was cooled to 0° C., 1M HCl was added, and the resulting mixture was allowed to warm to rt and stirred overnight. The reaction mixture was quenched with satd. aq. NaHCO3 and extracted with EtOAc. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent) to afford the title compound, 9a. m/z (ES) 417 (MH)+

Workup

  1. customthe resulting mixture was degassed
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. addition1M HCl was added
  4. temperatureto warm to rt
  5. customThe reaction mixture was quenched with satd
  6. extractionaq. NaHCO3 and extracted with EtOAc
  7. dry with materialThe combined organics were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-db2fefb1f8894dad9ac366a708c77e91
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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