Ethyl Acetate → HCID 58495533, compound

HRID 1191065Notes

Reaction equation

HRID 1191065 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][N:11]=1.CCOC(C)=O>CN(C=O)C.O>[CH3:8][O:7][C:5]([CH2:4][O:3][C:10]1[N:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=1)=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 50057186-Bromopyridine-3-carbonitrile

Product 1

HCID 58495533HCID 58495533, compoundYield 63%

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 methyl 2-hydroxyacetate (0.7 mL, 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 phase over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate (461 mg, 63%). MS (ES+) m/z: 193 (M+H)+.

Workup

  1. temperatureheat at 70° C. overnight
  2. dry with materialDry the organic phase 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-011a6c12de0f44febafe3f6c8710bd80
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…