HCID 11965617, compound → HCID 11965614, compound

HRID 906556Notes

Reaction equation

HRID 906556 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[CH:14]=[CH:13][O:12][CH:11]=2)[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH2:19]>C1COCC1.O.[Ni]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH2:19]

Participants

5

Reactant 1

HCID 11965617HCID 11965617, compound

Product 1

HCID 11965614HCID 11965614, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-5-furan-3-yl-4-trifluoromethyl-benzoic acid methyl ester (110 mg, 0.38 mmol) was dissolved in THF (15 mL) and, after addition of B113 W (Degussa) Ra/Ni (˜200 mg) in H2O the mixture was stirred for 26 d (TLC control) at 60° C. The mixture was filtered over Celite and evaporated under reduced pressure. The crude product was purified by flash chromatography with hexanes to hexanes/EtOAc 80:20 as eluent to furnish the title compound (51.3 mg, 46% yield) (290 [M+H]+, rt 5.52 min.).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. customevaporated under reduced pressure
  3. customThe crude product was purified by flash chromatography with hexanes to hexanes/EtOAc 80:20 as eluent

Sources & evidence

ORD record
ord-f6c36f927b91465ebcbe7e34523149db
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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