Potassium Carbonate → HCID 59852410, compound

HRID 1817156Notes

Reaction equation

HRID 1817156 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.CO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:6][N:7]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 59852410HCID 59852410, compoundYield 82.3%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-amino-6-bromopyrazine-2-carboxylate (0.116 g, 0.5 mmol), 3-fluorophenylboronic acid (0.14 g, 1.0 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.018 g, 0.02 mmol), and K2CO3 (0.14 g, 1.0 mmol) were combined in 3 mL of 4:1 CH3CN:H2O and heated to 150° C. for 10 minutes in the SmithSynthesizer microwave. Upon cooling, the reaction mixture was diluted with MeOH and H2O to dissolve all but the catalyst. The mixture was filtered and the pH was adjusted to 6 with 2N HCl. The solution was concentrated in vacuo, and the solids were collected to afford 3-amino-6-(3-fluorophenyl)pyrazine-2-carboxylic acid (96 mg) as a yellow solid.

Workup

  1. temperatureUpon cooling
  2. dissolutionto dissolve all but the catalyst
  3. filtrationThe mixture was filtered
  4. concentrationThe solution was concentrated in vacuo
  5. customthe solids were collected

Sources & evidence

ORD record
ord-67ed07a7694445b5b40b59e8bafd319e
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

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