Triethylamine → HCID 14042135, compound

HRID 2368225Notes

Reaction equation

HRID 2368225 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].[O:13]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14]1.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:15]2[CH:16]=[CH:17][O:13][CH:14]=2)[N:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 2734358Furan-3-boronic acid

Product 1

HCID 14042135HCID 14042135, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of palladium (II) acetate (145 mg, 0.65 mmol) and 1,1′-bis(diphenylphosphino)-ferrocene (493 mg, 0.86 mmol) in DMF (70 ml) was stirred at 50° C. for 15 minutes and cooled to r.t. The mixture was evacuated and vented with argon. 3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester (5.0 g, 21.5 mmol), furan-3-yl-boronic acid (2.79 g, 23.7 mmol) and triethylamine (4.51 ml, 32.3 mmol) were added and the reaction mixture was stirred at 90° C. for 16 h. The solvent was evaporated and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (2.92 g, 61.8%).

Workup

  1. temperaturecooled to r.t
  2. customThe mixture was evacuated
  3. stirringthe reaction mixture was stirred at 90° C. for 16 h
  4. customThe solvent was evaporated
  5. customthe product was obtained
  6. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-f9a66e228f954a249944cd75ca217071
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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