Allyl bromide → Allyl-[8-bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester

HRID 14478Notes

Reaction equation

HRID 14478 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][C:11]1[C:20]([Br:21])=[C:19]2[C:14]([C:15](=[O:32])[C:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[C:17]([CH:22]([CH3:24])[CH3:23])[O:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:40](Br)[CH:41]=[CH2:42]>CN(C)C=O.O>[CH2:1]([O:8][C:9](=[O:33])[N:10]([CH2:42][CH:41]=[CH2:40])[C:11]1[C:20]([Br:21])=[C:19]2[C:14]([C:15](=[O:32])[C:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[C:17]([CH:22]([CH3:24])[CH3:23])[O:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 68701803[8-Bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester

Product 1

HCID 68700441Allyl-[8-bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of [8-bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester (0.231 g, 0.44 mmol) and cesium carbonate (0.228 g, 0.701 mmol, 1.6 eq.) in N,N-dimethylformamide (10 ml) is treated with allyl bromide (0.058 g, 0.042 ml, 0.48 mmol, 1.1 eq.), and the mixture is stirred at room temperature for 4 h. The mixture is diluted with water and washed twice with ethyl acetate. The aqueous phase is additionally washed with methylene chloride. The combined organic phases are dried (magnesium sulfate) and filtered and the solvent is removed by evaporation in vacuo to afford the title compound as a yellow solid. The product is used in the next step without further purification.

Workup

  1. washwashed twice with ethyl acetate
  2. washThe aqueous phase is additionally washed with methylene chloride
  3. dry with materialThe combined organic phases are dried (magnesium sulfate)
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-eb404dd8ee424307974279854ddc9e94
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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