Benzyl Bromide → HCID 59163350, compound

HRID 1879117Notes

Reaction equation

HRID 1879117 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:23])=[C:6]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=2)=[O:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:23][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:7][C:6]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=1)=[O:9]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59163334HCID 59163334, compound

Product 1

HCID 59163350HCID 59163350, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl (4-{[(5-amino-2-chlorophenyl)carbonyl]amino}phenyl)acetate (300 mg, 0.90 mmol) in DMF (5 ml) was treated with potassium carbonate (152 mg, 1.1 mmol, 1.2 eq) and benzyl bromide (215 ul, 1.8 mmol, 2 eq) and stirred at room temperature overnight. The mixture was diluted with ethyl acetate (150 ml) and washed with water (2×80 ml) and brine (80 ml). Organic layer dried over magnesium sulphate and evaporated in vacuo. The residue was purified by column chromatography (Biotage SP4, 40 g silica column) eluting with 0-25% ethyl acetate in hexanes to afford the title compound as a white solid (90 mg). MS (ES+) m/z 423 [M+H]+ (C24H2335ClN2O3). 1H-NMR (400 MHz, d6-DMSO) δ 1.18 (3H, t, J 7.2), 3.61 (2H, s), 4.07 (2H, q, J 7.2), 4.30 (2H, d, J 6), 6.62-7.65 (13H, m).

Workup

  1. washwashed with water (2×80 ml) and brine (80 ml)
  2. dry with materialOrganic layer dried over magnesium sulphate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography (Biotage SP4, 40 g silica column)
  5. washeluting with 0-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a08b397192f244d1b4609bb4bca238f8
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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