Citric Acid → HCID 86619566, compound

HRID 1929821Notes

Reaction equation

HRID 1929821 reaction equation
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(COC)OC.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>[Br:9][C:5]1[N:6]=[C:7]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Cl:16])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 6200042-Amino-3,5-dibromopyrazineHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 86619566HCID 86619566, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.24 g) is added at room temperature to a solution of 2-amino-3,5-dibromopyrazine (0.51 g) in dimethoxyethane (12 mL). The mixture is stirred for 30 min and sodium carbonate (0.53 g), water (6 mL) and 2-chlorophenylboronic acid (0.32 g) are added and the mixture is stirred for 18 h at 100° C. The mixture is cooled, citric acid (10%, 20 mL) is added and the mixture is extracted with ethyl acetate (3×50 mL). Organic phases were pooled, washed with sodium bicarbonate and brine, dried with Na2SO4 and the solvent was evaporated. The residue was purified by chromatography on silica gel with dichloromethane to yield 0.31 g of the title compound as a white solid, mp 138.5-139.5° C.

Workup

  1. stirringthe mixture is stirred for 18 h at 100° C
  2. temperatureThe mixture is cooled
  3. extractionthe mixture is extracted with ethyl acetate (3×50 mL)
  4. washwashed with sodium bicarbonate and brine
  5. dry with materialdried with Na2SO4
  6. customthe solvent was evaporated
  7. customThe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-93f4dd944ffe48d8a0b894fbe5847d0e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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