p-Anisoyl chloride → 4-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)[CH3:15])=[C:4](F)[CH:3]=1.ClC1C=CC(C2C=CC=CC=2C(N)C)=C(F)C=1.C(N(CC)CC)C.COC1C=CC(C(Cl)=O)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([CH:14]([CH3:15])[N:16]([C:17]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)=[O:26])[C:4]=2[CH:3]=1)=[CH:10][CH:11]=[CH:12][CH:13]=3Participants
Procedure
N-[1-(4′-chloro-2′-fluoro-1,1′-biphenyl-2-yl)ethyl]-4-methoxybenzamide—The title compound was prepared from 1-(4′-chloro-2′-fluoro-biphenyl-2-yl)-ethylamine (1 g, 4 mmol), triethylamine (614 uL, 4.4 mmol), and 4-methoxybenzoyl chloride (683 mg, 4 mmol) according to the procedure and in the same manner as described in Example 24, step c. The crude residue was immediately purified on a Biotage® (40 Mi) column for flash column chromatography (5-30% methyl tert-butylether in hexane) resulting in the isolation of 1.22 g (79%) of a white solid. mp 165-165.9° C.; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (s, 3 H) 3.80 (s, 3 H) 4.94 (s, 1 H) 6.97 (d, J=8.79 Hz, 2 H) 7.15 (d, J=7.50 Hz, 1 H) 7.30 (s, 1 H) 7.43 (m, 2 H) 7.60 (m, 3 H) 7.82 (d, J=7.50 Hz, 2 H) 8.66 (s, 1 H). MS (ESI) m/z 384/386 ([M+H]+); Anal. calcd for C22H19ClFNO2: C:68.84 H:4.99 N:3.65 Found: C:68.81 H:5.07 N:3.65.
Workup
- customThe crude residue was immediately purified on a Biotage® (40 Mi) column for flash column chromatography (5-30% methyl tert-butylether in hexane)
Sources & evidence
- ORD record
- ord-f9cd7abd514b4bf3a7522b88be141811
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585871B2
Reaction notes
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