2-Furancarbonyl chloride → 7-Fluoro-2-(2-furyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17360Notes

Reaction equation

HRID 17360 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[C:3]=1[C:17]#[N:18].[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[F:9][C:6]1[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[C:3]([C:17]#[N:18])=[C:2]2[C:7]=1[O:8][C:24]([C:20]1[O:19][CH:23]=[CH:22][CH:21]=1)=[N:1]2

Participants

8

Reactant 4

HCID 682422-Furancarbonyl chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 685850137-Fluoro-2-(2-furyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 31%

Reagents, catalysts & solvents 3

HCID 7237O-XyleneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

4-Amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (100 mg, 0.41 mmol) was dissolved in xylene (10 ml), then at room temperature, triethylamine (70 μl), 2-furoyl chloride (49 μl, 0.50 mmol), pyridinium paratoluenesulfonate (31 mg, 0.12 mmol) were added. Next, this mixture liquid was stirred at 145° C. for 108 hours, then cooled to room temperature. This reaction liquid was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, this was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1), and the entitled compound (40 mg, 31%) was obtained as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. customThis reaction liquid
  3. customThe aqueous layer was separated
  4. extractionthis was extracted twice with ethyl acetate
  5. washthis was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe solvent was evaporated away
  9. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8dd7cb5e8c4a449e898d71d8de794471
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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