Ethyl Acetate → HCID 58495680, compound

HRID 1191063Notes

Reaction equation

HRID 1191063 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].Br[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=1.CCOC(C)=O>CN(C=O)C.O>[CH3:7][C:6]([CH3:9])([CH3:8])[C:5](=[O:10])[CH2:4][O:3][C:12]1[N:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 50057186-Bromopyridine-3-carbonitrileHCID 99558361-hydroxy-3,3-dimethylbutan-2-one

Product 1

HCID 58495680HCID 58495680, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve sodium hydride (380 mg, 9.5 mmol) in anhydrous DMF (7 mL). Cool at 0° C., add dropwise 1-hydroxy-3,3-dimethylbutan-2-one (1.1 g, 9.5 mmol) and stir at this temperature for 30 min. Add a solution of 6-bromo-nicotinonitrile in DMF (7 mL) and heat at 70° C. overnight. Cool the reaction mixture with ice/water and work-up sequentially with EtOAc and water. Dry the organic fraction over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate (424 mg, 50%). MS (ES+) if/A: 219 (M+H)+.

Workup

  1. temperatureheat at 70° C. overnight
  2. dry with materialDry the organic fraction over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-a6e097ca6b6f4fa78dff31b06b31f0ef
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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