Sodium Carbonate → HCID 11450797, compound

HRID 1975956Notes

Reaction equation

HRID 1975956 reaction equation
Br[C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:6][C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>C1(C)C=CC=CC=1.O.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>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:6][C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 11449803HCID 11449803, compound

Product 1

HCID 11450797HCID 11450797, compoundYield 63.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1.20 g (3.83 mmol) 5-bromo-N-methyl-2-(4-methyl-piperazin-1-yl)-isonicotinamide in 15 ml toluene were added successively 0.135 g tetrakis(triphenylphosphine)palladium(0), 4 ml 2 M sodium carbonate solution in water and 0.72 g (4.6 mmol) o-chlorphenylboronic acid. The mixture was heated under argon at 80° C. for 18 h. The aqueous layer was separated and washed with toluene. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.84 g (63%) of the title compound as a pale brown foam.

Workup

  1. customThe aqueous layer was separated
  2. washwashed with toluene
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-b9954f8a65914c23bdbd1ec79277d35c
Source dataset
uspto-grants-2001_05
Patent number
US06225316B1

Reaction notes

Loading…