Sodium Carbonate → 2'-Methyl-4'-(2-oxopyrrolidin-1-yl)[1,1'-biphenyl]-4-carboxylic acid

HRID 1274241Notes

Reaction equation

HRID 1274241 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][C:3]=1[CH3:14].B([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH3:14][C:3]1[CH:4]=[C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:6]=[CH:7][C:2]=1[C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 112189981-(4-bromo-3-methylphenyl)pyrrolidin-2-one

Product 1

HCID 230052992'-Methyl-4'-(2-oxopyrrolidin-1-yl)[1,1'-biphenyl]-4-carboxylic acidYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one (D12, 50 g, 0.20 mole) and 4-boronobenzoic acid (32 g, 0.20 mole) in DME (500 ml) was treated with a solution of sodium carbonate (94 g, 0.88 mole) in water (500 ml), then de-gassed by bubbling argon through for 0.25 hrs. Tetrakis (triphenylphosphine)palladium (0) (5 g) was added and the mixture heated under reflux for 22 hours, then allowed to cool and concentrated in vacuo to approx. 50% volume. The aqueous residue was diluted with water to approx. 1000 ml, washed with ethyl acetate, then acidified with conc. HCl acid. The precipitate was filtered off, washed with water, dried and recrystallised from ethanol to afford the title compound as a cream solid (30.3 g, 52%).

Workup

  1. customde-gassed
  2. customby bubbling argon through for 0.25 hrs
  3. additionTetrakis (triphenylphosphine)palladium (0) (5 g) was added
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 22 hours
  6. temperatureto cool
  7. concentrationconcentrated in vacuo to approx. 50% volume
  8. additionThe aqueous residue was diluted with water to approx. 1000 ml
  9. washwashed with ethyl acetate
  10. filtrationThe precipitate was filtered off
  11. washwashed with water
  12. customdried
  13. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-8e8394fc87a94105a60d02cf0fe6bf06
Source dataset
uspto-grants-2000_12
Patent number
US06156783

Reaction notes

Loading…