Potassium Carbonate → HCID 44252985, compound

HRID 1162191Notes

Reaction equation

HRID 1162191 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.C([O-])([O-])=O.[K+].[K+].[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>CC#N.O>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][N:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[CH2:32][C:31]1[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 66875540HCID 66875540, compound

Product 1

HCID 44252985HCID 44252985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

Intermediate B1 (480 mg, 1.5 mmoles) was dissolved in CH3CN (7.5 mL). Solid K2CO3 (518 mg, 3.75 mmoles), solid KI (250 mg, 1.5 mmoles) and neat 4-fluoro-benzyl-bromide (0.191 mL, 1.5 mmoles) were added, and the mixture was heated in a sealed vial in a microwave oven at 120° C. for 30+30 minutes. The reaction mixture was diluted with water (40 mL) and extracted with AcOEt (3×40 mL). The organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness. The crude was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 7/3). The title compound was obtained as a light-yellow solid in amount of 407 mg.

Workup

  1. extractionextracted with AcOEt (3×40 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 9/1 to 7/3)

Sources & evidence

ORD record
ord-3271127e6c2441a187df5a69a9bb08de
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

Loading…