Sodium Carbonate → HCID 19359116, compound

HRID 376760Notes

Reaction equation

HRID 376760 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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:8][C:5]1[N:4]=[CH:3][C:2]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([F:9])[C:15]=2[F:16])=[CH:7][N:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 2734333(2,3-Difluorophenyl)boronic acid

Product 1

HCID 19359116HCID 19359116, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A reaction of 288 mmol of 5-bromo-2-chloropyrimidine, 288 mmol of 2,3-difluorophenylboronic acid, 576 mmol of sodium carbonate and 5.8 mmol of tetrakis(triphenylphosphine)palladium(0) in 560 ml of toluene, 280 ml of ethanol and 280 ml of water is carried out analogously to the procedure indicated for precursor 3. Corresponding purification gives 37.7 g (58%) of a colorless solid.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-3f270311f04d49a88999c96b2d2edb4f
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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