Triphenylphosphine → HCID 59661993, compound

HRID 1959391Notes

Reaction equation

HRID 1959391 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[O:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1B(O)O.C([O-])(O)=O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(COC)OC.O.CCOC(C)=O.O.[Pd]>[O:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 6200042-Amino-3,5-dibromopyrazineHCID 2776266Benzo[b]furan-2-boronic acid

Product 1

HCID 59661993HCID 59661993, compoundYield 83.3%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 3,5-dibromopyrazin-2-amine (200 mg, 0.7908 mmol), benzofuran-2-ylboronic acid (140.9 mg, 0.8699 mmol), NaHCO3 (199.3 mg, 2.372 mmol) and palladium; triphenylphosphane (91.38 mg, 0.07908 mmol) in dimethoxyethane (2.000 mL) and water (1.000 mL) was heated at 120° C. in the microwave for 10 minutes. The reaction was diluted with EtOAc/Water and the layers separated. The aqueous layer was extracted further with EtOAc (2×), dried (MgSO4) and concentrated in vacuo. The mixture was purified on silica gel by flash column chromatography (0-20% EtOAc/Petrol) to afford the product as a bright yellow solid (191 mg, 83% Yield). MS (ES+) 291.89

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe mixture was purified on silica gel by flash column chromatography (0-20% EtOAc/Petrol)

Sources & evidence

ORD record
ord-ac145ad4a5874d9bb18fa7a35840391e
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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