2-Furancarbonyl chloride → HCID 68816228, compound

HRID 732552Notes

Reaction equation

HRID 732552 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:16]=[C:15]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[O:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:36](Cl)=[O:37].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:16]=[C:15]([C:36]([C:32]2[O:31][CH:35]=[CH:34][CH:33]=2)=[O:37])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68815098HCID 68815098, compound

Product 1

HCID 68816228HCID 68816228, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve N-methyl-N-propyl-5-tributylstannanyl-isophthalamic acid methyl ester (500 mg, 1 mmol), furan-2-carbonyl chloride (0.12 mL), tris(dibenzylideneacetone)-dipalladium (0) (19 mg) and 2-(di-tert-butylphosphino)biphenyl (35 mg) in THF (6 mL) in a previously degassed, sealed vessel. Flush the mixture with nitrogen and heat the sealed mixture overnight at 50° C. Cool the reaction to room temperature and filter though a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, 0:100 to 38:62 ethyl acetate:hexanes) to give the title compound (50%).

Workup

  1. customa previously degassed
  2. customsealed vessel
  3. customFlush the mixture with nitrogen
  4. temperatureCool
  5. customthe reaction to room temperature
  6. filtrationfilter though a filtering agent
  7. concentrationConcentrate the filtrate
  8. custompurify (silica gel chromatography, 0:100 to 38:62 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-42938261996d44a29db48e7f4aff0730
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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