3-Hydroxypyridine → HCID 55209004, compound

HRID 1908969Notes

Reaction equation

HRID 1908969 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[OH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 6933424-Chloro-2-pyridinecarbonitrile

Product 1

HCID 55209004HCID 55209004, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-pyridine carbonitrile (1.0 g, 7.2 mmol, 1.0 eq), 3-hydroxypyridine (686 mg, 7.21 mmol, 1.00 eq) and K2CO3 (1.2 g, 8.7 mmol, 1.2 eq) were dissolved in DMF (10 mL) and heated in a microwave for 15 minutes at 150° C. The reaction was cooled, diluted with EtOAc and washed with H2O (3×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 1.32 g (93%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.62 (d, J=5.8 Hz, 1H), 8.56 (m, 2H), 7.79 (d, J=2.4 Hz, 1H), 7.75 (dt, J=8.4, 1.4 Hz, 1H), 7.55 (dd, J=8.3, 4.7 Hz, 1H), 7.27 (dd, J=5.7, 2.4 Hz, 1H); ES-MS [M+1]+: 198.0.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with H2O (3×)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-73d310257bf3467ebdd83528767d406f
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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