Dimethylformamide → HCID 67307527, compound

HRID 1887452Notes

Reaction equation

HRID 1887452 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.I[C:21]1[CH:22]=[C:23]([CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1)[O:24][C:25]1[CH:26]=[N:27][CH:28]=[N:29][CH:30]=1.[CH3:37][N:38](C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[Zn+2].[C-]#N>[N+:34]([C:32]1[CH:33]=[C:21]([CH:22]=[C:23]([O:24][C:25]2[CH:26]=[N:27][CH:28]=[N:29][CH:30]=2)[CH:31]=1)[C:37]#[N:38])([O-:36])=[O:35]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 58337740HCID 58337740, compound

Product 1

HCID 67307527HCID 67307527, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of polymer-bound triphenylphosphine (170 mg, 0.437 mmol, 0.150 eq) and palladium(II) acetate (46 mg, 0.20 mmol, 0.070 eq) in DMF (8.7 mL) stirred under argon for 2 h at rt. The supernatant DMF was removed, and fresh DMF (8.7 mL) was added. Compound 20 (1.0 g, 2.9 mmol, 1.0 eq) and zinc cyanide (340 mg, 2.90 mmol, 1.00 eq) were added, and the vial was subjected to microwave irradiation at 150° C. for 25 minutes. The resin was washed with ether, and the collected filtrate was washed (3×) with water and (1×) with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 330 mg (47%) of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1H), 8.63 (s, 2H), 8.32 (t, J=1.4 Hz, 1H), 8.07 (t, J=2.2 Hz, 1H), 7.62 (dd, J=2.3, 1.3 Hz, 1H); ES-MS [M+1]+:243.0.

Workup

  1. customThe supernatant DMF was removed
  2. additionfresh DMF (8.7 mL) was added
  3. customirradiation at 150° C. for 25 minutes
  4. washThe resin was washed with ether
  5. washthe collected filtrate was washed (3×) with water and (1×) with brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1c05273c4927435c83d37a64a23ef602
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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