Dimethylformamide → HCID 52932843, compound

HRID 1665262Notes

Reaction equation

HRID 1665262 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][N:6]([C:8](=[O:25])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][C:18]=2[F:24])[CH:10]=1)[CH3:7])C.[F:27][C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:7][N:6]([CH2:5][C:4]([OH:3])=[O:26])[C:8](=[O:25])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:29]3[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:28]=3[F:27])=[CH:19][C:18]=2[F:24])[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27831332,4,5-Trifluorophenylboronic acidHCID 58271193HCID 58271193, compound

Product 1

HCID 52932843HCID 52932843, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of {{[3-(4-bromo-2-fluoro-phenoxymethyl)-benzoyl]-methyl-amino}-acetic acid ethyl ester (600 mg, 1.51 mmol), 2,4,5-trifluorophenylboronic acid (400 mg, 2.27 mmol), Pd(dppf)Cl2 methylene chloride complex (37 mg, 0.045 mmol), potassium carbonate (520 mg, 3.8 mmol), DMF (12 mL) and water (3 mL) was degassed, flashed with nitrogen, heated at 150° C. for 60 minutes in microwave reactor. The mixture was acidified by conc. HCl and diluted with water. Solvent was then removed by decantation and the sticky residue was purified by preparative HPLC to afford {{methyl-[3-(3,2′,4′,5′-tetrafluoro-biphenyl-4-yloxymethyl)-benzoyl]-amino}-acetic acid, 171 mg (25%). LC-MS (ES) calculated for C23H17F4NO4, 447; found m/z 448 [M+H]+.

Workup

  1. customwas degassed
  2. additiondiluted with water
  3. customSolvent was then removed by decantation
  4. customthe sticky residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a236e71750ed44619efa47c814c2a536
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

Loading…