Lithium Hexamethyldisilazide → 4-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol

HRID 731982Notes

Reaction equation

HRID 731982 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:26])[N:13]([C:16](=[O:25])[C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=4)[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.ClC1C=CC(C2C=CC=CC=2C(NC(=O)C2C=CC(OC)=CC=2)C)=C(F)C=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:26])[N:13]([C:16]([C:17]4[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=4)=[O:25])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 68814641N-[1-(4'-chloro-2'-fluoro-biphenyl-2-yl)-ethyl]-4-methoxy-benzamideHCID 688171033-Chloro-5-(4-methoxybenzoyl)-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 116603034-[(3-chloro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-chloro-5-(4-methoxybenzoyl)-6-methyl-5,6-dihydrophenanthridine—The title compound was prepared from N-[1-(4′-chloro-2′-fluoro-biphenyl-2-yl)-ethyl]-4-methoxy-benzamide (1.04 g, 2.7 mmol), anhydrous THF (10 mL), and lithium bis(trimethylsilyl)amide (4.1 mL, 1M in THF) according to the procedure and in the same manner as described in Example 24, step d. The THF was removed and the resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane) affording 738 mg (75%) of the desired product. MS [(ES+), m/z]: 364/366 [M+H]+, 1 Cl pattern;

Workup

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

Sources & evidence

ORD record
ord-c4e5084e815c418ca11f249f5ff49559
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Reaction notes

Loading…