Toluene → 2,4'-Dimethyl-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxylic acid

HRID 1845205Notes

Reaction equation

HRID 1845205 reaction equation
I[C:2]1[C:3]([CH3:19])=[C:4]([CH:8]=[C:9]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].B(O)(O)[C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH3:19][C:3]1[C:4]([C:5]([OH:7])=[O:6])=[CH:8][C:9]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:10][C:2]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 581883403-Iodo-2-methyl-5-(pyrrolidin-1-ylsulfonyl)benzoic acid

Product 1

HCID 581880832,4'-Dimethyl-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-iodo-2-methyl-5-(pyrrolidin-1-ylsulfonyl)benzoic acid (1.00 g, 2.53 mmol), p-tolylboronic acid (0.378 g, 2.78 mmol), toluene (10 mL), ethanol (3 mL), cesium carbonate (0.907 g, 2.78 mmol), and water (1 mL) under argon was added tetrakis(triphenylphosphine)palladium(0) (146 mg, 0.126 mmol). The mixture was heated to reflux for 6 h, and then cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified by silica gel column (0-50% EtOAc/hexane) to yield a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column (0-50% EtOAc/hexane)
  6. customto yield a yellow solid

Sources & evidence

ORD record
ord-94754504cb064c59999fbde58b2c1f9b
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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