Dimethylformamide → HCID 58318794, compound

HRID 2401501Notes

Reaction equation

HRID 2401501 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([O:31][C:32]2[CH:33]=[N:34][CH:35]=[N:36][CH:37]=2)[CH:30]=1)[C:24]([O:26][CH3:27])=[O:25].[CH3:38][N:39](C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[Zn+2].[C-]#N>[C:38]([C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([O:31][C:32]2[CH:33]=[N:34][CH:35]=[N:36][CH:37]=2)[CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])#[N:39]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 58318830HCID 58318830, compound

Product 1

HCID 58318794HCID 58318794, compoundYield 32%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of polymer-bound triphenylphosphine (18 mg, 0.047 mmol, 0.15 eq) and palladium(II) acetate (5.0 mg, 0.022 mmol, 0.07 eq) in DMF (1.0 mL) stirred under argon at rt for 2 h. The supernatant DMF was removed, and fresh DMF (1.0 mL) was added. Methyl 3-bromo-5-(pyrimidin-5-yloxy)benzoate (96 mg, 0.31 mmol, 1.0 eq) and zinc cyanide (37 mg, 0.31 mmol, 1.0 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 25 mg (32%) of the title compound as a clear oil: 1H NMR (400 MHz, DMSO-d6) δ 9.09 (s, 1H), 8.76 (s, 2H), 8.16 (s, 1H), 8.07 (dd, J=2.3, 1.3 Hz, 1H), 7.91 (dd, J=2.3, 1.4 Hz, 1H), 3.88 (s, 3H); ES-MS [M+1]+:256.1.

Workup

  1. customThe supernatant DMF was removed
  2. additionfresh DMF (1.0 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-90245bbe8357478eab96b888ff46bec6
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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