Sodium Carbonate → HCID 46834571, compound

HRID 2204779Notes

Reaction equation

HRID 2204779 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:31][C:32]1[C:33]([C:39]([NH:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:40])=[N:34][C:35](Br)=[CH:36][N:37]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd]Cl>[NH2:31][C:32]1[C:33]([C:39]([NH:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:40])=[N:34][C:35]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:36][N:37]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 201262(4-Methoxyphenyl)boronic acidHCID 529371483-amino-6-bromo-N-phenylpyrazine-2-carboxamide

Product 1

HCID 46834571HCID 46834571, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
88 °C

Procedure

A Greenhouse tube was charged with 4-Methoxyphenylboronic acid (31.4 mg, 0.207 mmol) and treated with a solution of dichloropalladium; triphenylphosphane (4.84 mg, 0.0069 mmol) and 3-amino-6-bromo-N-phenyl-pyrazine-2-carboxamide (40.45 mg, 0.138 mmol) in DMF (0.81 mL) followed by Na2CO3 (2M solution, 207 uL, 0.414 mmol). The mixture was flushed with nitrogen and heated to 88° C. for 18 hours. After this time the reaction was filtered to remove inorganics and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were freeze-dried to give the title compound as a solid (18.56 mg, 38% Yield). MS (ES+) 321

Workup

  1. customThe mixture was flushed with nitrogen
  2. filtrationAfter this time the reaction was filtered
  3. customto remove inorganics
  4. customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  5. customThe fractions were freeze-dried

Sources & evidence

ORD record
ord-8391187e7d604dd5a0981df1524ec3b6
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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