Triphenylarsine → HCID 22674384, compound

HRID 1005714Notes

Reaction equation

HRID 1005714 reaction equation
C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[C:25]2[N:26]=[C:27]([N:37]([CH3:39])[CH3:38])[N:28]=[C:29]([C:30]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[O:31])[C:24]=2[S:23][CH:22]=1.C([Sn](CCCC)(CCCC)[C:45]1[O:46][CH:47]=[CH:48][CH:49]=1)CCC.[NH4+].[Cl-]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][N:37]([CH3:39])[C:27]1[N:28]=[C:29]([C:30]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[O:31])[C:24]2[S:23][CH:22]=[C:21]([C:45]3[O:46][CH:47]=[CH:48][CH:49]=3)[C:25]=2[N:26]=1

Participants

7

Reactant 4

HCID 11773TriphenylarsineHCID 25517Ammonium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 22674498HCID 22674498, compound

Product 1

HCID 22674384HCID 22674384, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of palladium(II) acetate (4.1 mg, 18.3 μmol) and triphenylarsine (22.4 mg, 73 μmol) in DMF (0.8 mL) was stirred under an atmosphere of argon at room temperature for 10 min, treated with a solution of 7-bromo-2-dimethylaminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.067 g, 0.18 mmol) in DMF (1.1 mL), stirred for 10 min then treated dropwise with 2-tri-n-butylstannylfuran (104 μL, 0.33 mmol). The reaction mixture was stirred at 100° C. for 117 h, cooled, poured into saturated NH4Cl (5 mL), extracted with EtOAc (4×5 mL), the combined organic phase washed with water (5 mL), dried (MgSO4), concentrated in vacuo and the resulting residue purified by chromatography [SiO2; heptane-EtOAc (100:0-95:5 gradient)] to give the title compound (57 mg, 87%) as an orange solid.

Workup

  1. stirringstirred for 10 min
  2. stirringThe reaction mixture was stirred at 100° C. for 117 h
  3. temperaturecooled
  4. extractionextracted with EtOAc (4×5 mL)
  5. washthe combined organic phase washed with water (5 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customthe resulting residue purified by chromatography [SiO2; heptane-EtOAc (100:0-95:5 gradient)]

Sources & evidence

ORD record
ord-65cebc84acdc49c5b766b078fdd72b5c
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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