Trifluoroacetic acid → HCID 4763727, compound

HRID 382179Notes

Reaction equation

HRID 382179 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.CO[CH:23]1[CH2:27][CH2:26][CH:25](OC)O1>ClCCCl>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:3][C:2]([N:1]2[CH:23]=[CH:27][CH:26]=[CH:25]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 71024-AminobiphenylHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 4763727HCID 4763727, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-aminobiphenyl (1.0 g, 5.9 mmol) in 1, 2-dichloroethane (20 mL) was added TFA (0.46 ml, 5.9 mmol). To the resultant suspension of the TFA salt was added 2,5-dimethoxy-tetrahydrofuran (0.92 mL, 7.1 mmol). The suspension was heated at 75° C. for 17 hours. The mixture was allowed to cool, partitioned between EtOAc and 1M pH 7 phosphate buffer, and the aqueousueous layer was extracted again with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to a crude residue, which was purified via flash column chromatography with 10-25% CH2Cl2/hex gradient eluent. The purified material was triturated with MTBE/hex to give 800 mg (62%) of N-biphenyl-4-yl-1H-pyrrole as an off-white solid, mp190-2° C.

Workup

  1. temperatureto cool
  2. custompartitioned between EtOAc and 1M pH 7 phosphate buffer
  3. extractionthe aqueousueous layer was extracted again with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to a crude residue, which
  6. customwas purified via flash column chromatography with 10-25% CH2Cl2/hex gradient eluent
  7. customThe purified material was triturated with MTBE/hex

Sources & evidence

ORD record
ord-917357f14043401c83b86d01baca66f0
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

Loading…