Lithium Hexamethyldisilazide → 5,7-dibromo-3-methyl-3-phenyl-1H-quinoline-2,4-dione

HRID 735239Notes

Reaction equation

HRID 735239 reaction equation
CO[C:3](=[O:23])[C:4]1[C:9]([Br:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:22])[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CCOC(C)=O>[Br:10][C:9]1[CH:8]=[C:7]([Br:11])[CH:6]=[C:5]2[C:4]=1[C:3](=[O:23])[C:14]([CH3:15])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:13](=[O:22])[NH:12]2

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 688165794,6-Dibromo-2-(2-phenyl-propionylamino)-benzoic acid methyl ester

Product 1

HCID 115677165,7-dibromo-3-methyl-3-phenyl-1H-quinoline-2,4-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 4,6-dibromo-2-(2-phenyl-propionyl amino)-benzoic acid methyl ester (1.00 g, 2.27 mmol) and LiHMDS (6.81 mmol, 1M THF solution). After normal workup, the pure objective compound (0.60 g, 65%) was obtained as yellow solid by a flash column chromatography (Hex:EtOAc=4:1): 1H NMR (200 MHz, CDCl3) δ 1.64 (s, 3H, CH3), 7.04 (d, J=1.6 Hz, 1H, ArH), 7.17-7.37 (m, 5H, ArH), 7.46 (d, J=1.6 Hz, 1H, ArH), 9.35 (br s, 1H, NH); m.p. 202-203° C.; MS(EI) m/e 409 [M+], 288, 132, 104; HRMS m/e cacld. for C16H11Br2NO2 406.9157, found 406.9161.

Workup

  1. customThe objective compound was prepared by the same procedure for the example 1

Sources & evidence

ORD record
ord-61265bc6f5df44acabce1d0ca5bd7d4e
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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