Ethyl Acetate → 2-(3-Pyridyl)-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062672Notes

Reaction equation

HRID 1062672 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:18]([NH2:26])(=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.C(OCC)(=O)C>O1CCCC1>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:18]2[S:25][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=3)[N:26]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 737155ThionicotinamideHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

Product 1

HCID 222824922-(3-Pyridyl)-4-(3-cyanophenyl)-5-carboethoxythiazoleYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (1.0 g, 3.4 mmol) in 20 mL of tetrahydrofuran was added thionicotinamide (0.46 g, 3.4 mmol). The resulting mixture was stirred at 65° C. for 16 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was triturated with chloroform, taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with ethyl acetate left the title compound as an off-white solid (0.26 g, 23%). MS (ESI) 336.1 (M+H)+.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with chloroform
  4. washwashed with saturated aq Na2CO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a solid

Sources & evidence

ORD record
ord-0749c6ecbf2a4083aea68fb0a614a07c
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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