Butyl vinyl ether → HCID 16073198, compound

HRID 915514Notes

Reaction equation

HRID 915514 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:20][CH:21](C)C)[C:12](N3CCOCC3)=[CH:13][C:8]=2[O:7][C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4].[CH:31]1[CH:36]=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:32]=1.C([O:62]CCCC)=C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:20][CH3:21])[C:12]([C:31]([OH:62])([CH3:36])[CH3:32])=[CH:13][C:8]=2[O:7][C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4]

Participants

7

Reactant 4

HCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 10047296HCID 10047296, compound

Product 1

HCID 16073198HCID 16073198, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Preparation of compound 49(a) (6-acetyl-2-(4-fluoro-phenyl)-5-isopropoxy-benzofuran-3-carboxylic acid methylamide). A sealed tube was charged with magnetic stirrer, compound 24(b) (1.22 g, 3.0 mmol, which can be prepared according to Example 24, step b above), palladium(II) acetate (34 mg, 0.015 mmol), [1,1′-bis(diphenylphosphino)propane] (DPPP) (136 mg, 0.33 mmol), butyl vinyl ether (1.92 mL, 15 mmol), and K2CO3 (622 mg, 4.5 mmol) in DMF (5 mL). The tube was flushed with argon, sealed, and heated to 100° C. for 24 hours, then cooled to room temperature. 5% HCl (20 mL) was added dropwise over 20 minutes, and the mixture with extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 20% ethyl acetate in hexanes) to yield 0.94 g (85%) of the desired product.

Workup

  1. additionA sealed tube was charged with magnetic stirrer
  2. customThe tube was flushed with argon
  3. customsealed
  4. temperaturecooled to room temperature
  5. addition5% HCl (20 mL) was added dropwise over 20 minutes
  6. extractionthe mixture with extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography (silica gel, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c395e59624884f92b3cb31f3d2ef70ab
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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