Dimethylformamide → HCID 58349269, compound

HRID 1908973Notes

Reaction equation

HRID 1908973 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([O:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:26]=1.[CH3:34][N:35](C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[Zn+2].[C-]#N>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([O:27][C:25]2[CH:24]=[N:23][CH:22]=[C:21]([CH:26]=2)[C:34]#[N:35])[CH:29]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 219640523-Bromo-5-[(pyridin-3-yl)oxy]pyridine

Product 1

HCID 58349269HCID 58349269, compoundYield 100%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of polymer-bound triphenylphosphine (230 mg, 0.597 mmol, 0.150 eq) and palladium(II) acetate (63 mg, 0.28 mmol, 0.070 eq) in DMF (12 mL) stirred under argon at rt for 2 h. The supernatant DMF was removed, and fresh DMF (12 mL) was added. Compound 4 (1.0 g, 3.9 mmol, 1.0 eq) and zinc cyanide (470 mg, 4.00 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 780 mg (100%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.84 (d, J=1.4 Hz, 1H), 8.74 (d, J=2.8 Hz, 1H), 8.51 (d, J=2.8 Hz, 1H), 8.47 (d, J=4.6 Hz, 1H), 8.13 (t, J=2.1 Hz, 1H), 7.63 (ddd, J=8.4, 2.7, 1.1 Hz, 1H), 7.49 (dd, J=8.5, 4.6 Hz, 1H); ES-MS [M+1]+:198.1.

Workup

  1. customThe supernatant DMF was removed
  2. additionfresh DMF (12 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-bfaf1215dd08443380b93b34d40255f7
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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