Water → HCID 68669944, compound

HRID 2070952Notes

Reaction equation

HRID 2070952 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[N:5]=[C:4]([C:12]([OH:15])([CH3:14])[CH3:13])[CH:3]=1.[C:16]([Cu])#[N:17].O.CCOC(C)=O>CN(C=O)C>[OH:15][C:12]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[N:5]=1)[C:16]#[N:17])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 68671820HCID 68671820, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68669944HCID 68669944, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.45 g (5.28 mmol) of 2,2′-(4-bromopyridine-2,6-diyl)dipropan-2-ol and 585 mg (6.53 mmol) of CuCN in 20 mL of DMF was heated at 150° C. After about 20.5 h, 40 mL of H2O and EtOAc was added, and the mixture was filtered through a Buchner funnel. The layers were separated, and the organic layer was washed with water (3×30 mL) and brine (30 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1% MeOH/CHCl3) provided 373 mg of 2,6-bis(2-hydroxypropan-2-yl)isonicotinonitrile as a pale orange solid in 32% yield.

Workup

  1. filtrationthe mixture was filtered through a Buchner funnel
  2. customThe layers were separated
  3. washthe organic layer was washed with water (3×30 mL) and brine (30 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (1% MeOH/CHCl3)

Sources & evidence

ORD record
ord-9914ab18f6394a56b1d4d277647a9777
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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