Hexane → HCID 11562119, compound

HRID 735254Notes

Reaction equation

HRID 735254 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([Br:11])[C:5]=1[NH:12][C:13](=[O:27])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[Br:10][C:8]1[CH:9]=[C:4]2[C:5](=[C:6]([Br:11])[CH:7]=1)[NH:12][C:13](=[O:27])[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1)([CH3:15])[C:3]2=[O:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 68820138HCID 68820138, compound

Product 1

HCID 11562119HCID 11562119, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 3,5-dibromo-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl ester (0.65 g, 1.26 mmol) and LiHMDS (3.78 mmol, 1M solution in THF). After normal workup, the objective compound (160 mg, 27%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=2:1): 1H NMR (200 MHz, DMSO-d6) δ 1.68 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 7.32 (d, J=9.0 Hz, 1H, ArH), 7.43 (dd, J=8.8, 2.4 Hz, 1H, ArH), 7.69 (d, J=2.4 Hz, 1H, ArH), 7.84 (d, J=2.6 Hz, 1H, ArH), 8.12 (d, J=2.6 Hz, 1H, ArH); MS(EI) m/e 482 [M+], 277, 207, 102 ; HRMS m/e cacld. for C17H12N2O5Br2 481.9113, found 481.9122.

Workup

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

Sources & evidence

ORD record
ord-4e0f4eb1b54d448a9996d9e9a194473b
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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