Butyl vinyl ether → HCID 16073198, compound

HRID 1445526Notes

Reaction equation

HRID 1445526 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 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 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-45f9bd7823cf452a814e381f2f588e98
Source dataset
uspto-grants-2010_02
Patent number
US07666863B2

Reaction notes

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