Benzyl Alcohol → [8-Bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester

HRID 14477Notes

Reaction equation

HRID 14477 reaction equation
[NH2:1][C:2]1[C:11]([Br:12])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([CH:13]([CH3:15])[CH3:14])[O:9]2)=[CH:4][CH:3]=1.[C:24](Cl)(Cl)=[O:25].C(N(CC)CC)C.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:35]([O:42][C:24](=[O:25])[NH:1][C:2]1[C:11]([Br:12])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[C:8]([CH:13]([CH3:14])[CH3:15])[O:9]2)=[CH:4][CH:3]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 6371PhosgeneHCID 8471TriethylamineHCID 597242447-Amino-8-bromo-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Product 1

HCID 68701803[8-Bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 7-amino-8-bromo-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one (0.242 g, 0.62 mmol) in anhydrous methylene chloride (5 ml) is treated with a 20% solution of phosgene in toluene (0.5 ml). After 3 h, triethylamine (0.12 g, 0.17 ml, 1.24 mmol, 2 eq.) is added, followed by benzyl alcohol (0.067 g, 0.064 ml, 0.62 mmol), and the solution is stirred at room temperature overnight. The solution is diluted with methylene chloride and washed with water. The organic layer is dried (magnesium sulfate) and filtered, and the solvent is removed by evaporation in vacuo. The resulting solid is purified by flash chromatography (cyclohexane/ethyl acetate=9:1) to afford the title compound as a pale yellow solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent is removed by evaporation in vacuo
  5. customThe resulting solid is purified by flash chromatography (cyclohexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-398268ad58a94c6b93819e262fefdffd
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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