Lithium Hexamethyldisilazide → 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].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[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
Procedure
3-fluoro-5-(4-methoxybenzoyl)-6-methyl-5,6-dihydrophenanthridine—_The title compound was prepared from N-[1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethyl]-4-methoxybenzamide (1.29 g, 3.5 mmol), anhydrous THF (10 mL), and lithium bis(trimethylsilyl)amide (4.0 mL, 1M in THF) according to the procedure and in the same manner as described in Example 33, step d. The residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane) affording 1.1 g (90%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.76 Hz, 3 H) 3.77 (s, 3 H) 5.68 (q, J=6.67 Hz, 1 H) 6.60 (dd, J=10.39, 2.60 Hz, 1 H) 6.90 (d, J=8.84 Hz, 2 H) 7.07 (td, J=8.64, 2.73 Hz, 1 H) 7.27 (d, J=8.58 Hz, 2 H) 7.40 (m, 3 H) 7.97 (m, 1 H) 8.00 (dd, J=8.84, 6.24 Hz, 1 H); MS (ESI) m/z 348 ([M+H]+); HRMS: calcd for C22H18FNO2, 347.1322 (M), 348.13944 ([M+H]+); found (ESI_FT), 348.13914.
Workup
- customThe residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane)
Sources & evidence
- ORD record
- ord-b41803be3cfc4c48918a774722ccea44
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585871B2
Reaction notes
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