p-Anisoyl chloride → 4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol
Reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([NH:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)[CH3:16].COC1C=CC(C(Cl)=O)=CC=1.FC1C=C(F)C=CC=1C1C=CC=CC=1C(N)C.C(N(CC)CC)C>CCCCCC.COC(C)(C)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]3[C:10]([CH:15]([CH3:16])[N:17]([C:18]([C:19]4[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=4)=[O:27])[C:2]=2[CH:7]=1)=[CH:11][CH:12]=[CH:13][CH:14]=3Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
N-[1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethyl]-4-methoxybenzamide—The title compound was prepared from 4-methoxybenzoyl chloride (731 mg, 4.28 mmol), 1-(-2′,4′-difluoro-biphenyl-2-yl)-ethylamine (1 g, 4.28 mmol), and triethylamine (717 uL, 5.1 mmol) according to the procedure and in the same manner as described in Example 33, step c. The product was isolated from a Biotage® (40 Mi) column for flash column chromatography (5-30% methyl tert-butylether in hexane) resulting in the isolation of a white solid, 1.53 g (97%). mp 134.5-135° C.; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (d, J=5.43 Hz, 3 H) 3.80 (s, 3 H) 4.96 (m, J=5.95 Hz, 1 H) 6.97 (d, J=9.05 Hz, 2 H) 7.18 (m, 2 H) 7.36 (m, 3 H) 7.64 (d, J=4.14 Hz, 2 H) 7.83 (d, J=7.50 Hz, 2 H) 8.66 (s, 1 H); MS (ESI) m/z 368 ([M+H]+); Anal. calcd for C22H19F2NO2: C:71.92 H:5.21 N:3.81 Found: C:72.11 H:5.23 N:3.77
Workup
- customresulting in the isolation of a white solid, 1.53 g (97%)
Sources & evidence
- ORD record
- ord-3f2ccc82aa80439f8eb29f9c9b3dd79a
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585871B2
Reaction notes
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