Dimethylformamide → HCID 22735171, compound

HRID 50572Notes

Reaction equation

HRID 50572 reaction equation
[CH:1]1[CH:6]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:2]=1.Br[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:26]=1.CN(C=[O:37])C>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]1[CH:26]=[C:21](/[CH:2]=[CH:1]/[CH:6]=[O:37])[CH:22]=[N:23][CH:24]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 227351815'-Bromo-2,3'-bipyridine

Product 1

HCID 22735171HCID 22735171, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of Pd2(dba)3 (36 mg, 0.04 mmol) and PPh3 (triphenylphosphine) in DMF (degassed, 2.0 mL) was allowed to stir for 5 min. at 25° C. 1,1′-Diethyl 3-(tributyltin)-propenylacetal (0.44 g, 1.27 mmol) and 3-bromo-5-(2-pyridinyl)-pyridine (100 mg, 0.42 mmol) were added and the resulting mixture was warmed to 80° C. After 18 h, the reaction mixture was allowed to cool to 25° C., diluted with ethyl acetate (100 mL), washed with brine (1×50 mL) and concentrated in vacuo. The residue was dissolved in 2N aqueous HCl (2.0 mL) and allowed to stir for 30 min. The reaction mixture was neutralized by the addition of sodium bicarbonate until the pH ˜7, diluted with ethyl acetate (100 mL), washed with brine (1×50 mL), and concentrated in vacuo. Purification by flash chromatography (0-50% EtOAc/hexanes) afforded the title compound (10 mg) as a white solid. MS 211 (M+H)+.

Workup

  1. temperaturethe resulting mixture was warmed to 80° C
  2. waitAfter 18 h
  3. temperatureto cool to 25° C.
  4. washwashed with brine (1×50 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 2N aqueous HCl (2.0 mL)
  7. stirringto stir for 30 min
  8. additionThe reaction mixture was neutralized by the addition of sodium bicarbonate until the pH ˜7
  9. additiondiluted with ethyl acetate (100 mL)
  10. washwashed with brine (1×50 mL)
  11. concentrationconcentrated in vacuo
  12. customPurification by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ee06eb1885d14711ab40a55ff4ced6ab
Source dataset
uspto-grants-2004_03
Patent number
US06713455B2

Reaction notes

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