Triethylamine → HCID 67345264, compound

HRID 1260281Notes

Reaction equation

HRID 1260281 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(N(CC)CC)C>CN(C=O)C>[N+:12]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[NH:22][C:21]1[CH:23]=[CH:24][C:18]([O:17][C:16]([F:15])([F:25])[F:26])=[CH:19][CH:20]=1)[C:6]([O:8][CH3:9])=[O:7])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6008484-(Trifluoromethoxy)anilineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 67345264HCID 67345264, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of methyl 4-fluoro-3-nitrobenzoate (853 mg, 4.28 mmol), 4-trifluoromethoxyaniline (759 mg, 4.28 mmol) and triethylamine (1.79 mL, 12.9 mmol) in DMF (5.00 mL) was heated to 70° C. for 24 h. The reaction mixture was concentrated in vacuo, and the resulting crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-10% methanol/DCM as eluent) afforded the title compound i-3a. m/z (ES) 357 (MH)+. 1H NMR (500 MHz, CDCl3): δ 9.77 (s, 1H), 8.96 (s, 1H), 8.03 (d, 1H, J=8.5 Hz), 7.34 (m, 4H), 7.16 (d, 1H, J=8.5 Hz), 3.95 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-10% methanol/DCM as eluent)

Sources & evidence

ORD record
ord-6c98979d34e94b76959ac5db59308f33
Source dataset
uspto-grants-2013_06
Patent number
US08470819B2

Reaction notes

Loading…