Sodium Carbonate → N-methyl-6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamide

HRID 379370Notes

Reaction equation

HRID 379370 reaction equation
I[C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:25]1([CH3:34])[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>C1(C)C=CC=CC=1.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>[CH3:11][NH:10][C:8](=[O:9])[C:7]1[C:2]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH3:34])=[CH:3][C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 184033594-iodo-N-methyl-6-(4-methyl-piperzin-1-yl)-nicotinamide

Product 1

HCID 15481065N-methyl-6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamideYield 63%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 4.00 g (11.1 mmol) 4-iodo-N-methyl-6-(4-methyl-piperzin-1-yl)-nicotinamide and 642 mg (0.555 mmol) tetrakis(triphenylphosphine)palladium(0) in 60 ml toluene was dioxygenated with a stream of argon for 30 min. After addition of 11 ml of a 2 N aqueous solution of sodium carbonate and 1.66 g (12.2 mmol) o-tolylboronic acid, the mixture was heated at reflux overnight. Cooling to room temperature was followed by dilution with water and extraction with three 50 ml portions of ethyl acetate. The aqueous layer was saturated with sodium chloride and extracted with three 50 ml portions of dichloromethane. The combined organic layers were dried with sodium sulfate and concentrated. Column chromatography afforded 2.26 g (63%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. extractionwas followed by dilution with water and extraction with three 50 ml portions of ethyl acetate
  4. extractionextracted with three 50 ml portions of dichloromethane
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-295de8ae5d17475aabcf27212d0eb0c5
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

Loading…