Potassium Carbonate → HCID 23400762, compound

HRID 1062912Notes

Reaction equation

HRID 1062912 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.[C:16]([O:20][C:21]([NH:23][C:24]1([CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([OH:48])[CH:43]=3)=[CH:37][CH:36]=2)[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[O:26][CH2:25]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([O:20][C:21]([NH:23][C:24]1([CH2:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH2:12][C:11]4[CH:14]=[CH:15][C:8]([Cl:7])=[CH:9][CH:10]=4)[CH:43]=3)=[CH:39][CH:40]=2)[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[O:26][CH2:25]1)=[O:22])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 23400763HCID 23400763, compound

Product 1

HCID 23400762HCID 23400762, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (150 mg) and p-chlorobenzyl bromide (103 mg) were added to a DMF solution (5 mL) of the compound of Example 105 (150 mg) and the mixture was stirred for 1 hour at 70° C. Subsequently, the mixture was decanted into water and was extracted with ethyl acetate. The organic phase was sequentially washed with water and a saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the desired product (170 mg) as a colorless powder.

Workup

  1. customSubsequently, the mixture was decanted into water
  2. extractionwas extracted with ethyl acetate
  3. washThe organic phase was sequentially washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0e09703f97204ad5ba13e7a2d130ba8b
Source dataset
uspto-grants-2005_11
Patent number
US06963012B2

Reaction notes

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