Triphenylarsine → HCID 11610887, compound

HRID 2233762Notes

Reaction equation

HRID 2233762 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3I)[N:9]([CH2:17][C:18]([O:20]CC)=[O:19])[C:8]=2[CH3:23])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:31]1[CH:36]=[N:35][CH:34]=[CH:33][N:32]=1)CCC.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O.[Pd].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:31]3[CH:36]=[N:35][CH:34]=[CH:33][N:32]=3)[N:9]([CH2:17][C:18]([OH:20])=[O:19])[C:8]=2[CH3:23])=[CH:24][CH:25]=1

Participants

9

Reactant 4

HCID 11773TriphenylarsineHCID 14798Sodium HydroxideHCID 27373162-(Tributylstannyl)pyrazineHCID 86609240HCID 86609240, compound

Product 1

HCID 11610887HCID 11610887, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

The product from step (i) (250 mg), 2-(tributylstannyl)-pyrazine (260 mg), Pd (dba)2 (30 mg) and triphenyl-arsine (210 mg) were dissolved in toluene (4 ml) and heated at 90° C. for 20 h. The reaction was cooled to RT, methanol (10 ml) added, followed by 1M aqueous sodium hydroxide (2 ml) and stirred for 20 h. The mixture was diluted with water, extracted with EtOAc, washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified using reverse phase preparative chromatography (eluent MeCN/NH3(aq)) to give the title compound. Yield 30 mg.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-fc6d70a47e4c487783a083bfd489713c
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

Loading…