Lithium Hexamethyldisilazide → 4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diol

HRID 731994Notes

Reaction equation

HRID 731994 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:28])[N:13]([C:16](=[O:27])[C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=4[O:25]C)[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.FC1C=C(F)C=CC=1C1C=CC=CC=1C(NC(=O)C1C=CC(OC)=CC=1OC)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:28])[N:13]([C:16]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=4[OH:25])=[O:27])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 688162733-Fluoro-5-(2,4-dimethoxybenzoyl)-6-methyl-5,6-dihydrophenanthridineHCID 68816650N-[1-(2',4'-difluoro-1,1'-biphenyl-2-yl)ethyl]-2,4-dimethoxybenzamide

Product 1

HCID 115303814-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-fluoro-5-(2,4-dimethoxybenzoyl)-6-methyl-5,6-dihydrophenanthridine—The title compound was prepared from N-[1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethyl]-2,4-dimethoxybenzamide (1.29 g, 3.2 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 resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane) affording 1.2 g (99%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (d, J=6.76 Hz, 3 H) 3.79 (br m, 6 H) 3.92 (s, 1 H) 6.28 (s, 1 H) 6.62 (m, 1H) 7.06 (s, 1 H) 7.34 (br m, 1 H) 7.42 (br m, 3 H) 7.52 (br d, J=7.54 Hz, 1 H) 7.96 (m, 2 H); MS (ESI) m/z 378 ([M+H]+); HRMS: calcd for C23H20FNO3, 377.1427 (M), 378.15000 ([M+H]+); found (ESI_FT), 378.14878

Workup

  1. customThe resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane)

Sources & evidence

ORD record
ord-e47b21d3c4a6454ab5d586ca87871ba3
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Reaction notes

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