Ethyl bromopyruvate → HCID 59251444, compound

HRID 1466412Notes

Reaction equation

HRID 1466412 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[NH:8])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:24][C:25](=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(O)(C)C>[CH2:29]([O:28][C:26]([C:25]1[N:8]=[C:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)[N:9]([C:10]2[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=2[Cl:16])[CH:24]=1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178512060HCID 178512060, compound

Product 1

HCID 59251444HCID 59251444, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

A stirred mixture of 5-bromo-N-(2,6-dichlorophenyl)-thiophene-2-carboxamidine (3.9 g, 11 mmol) and sodium bicarbonate (1.85 g, 22 mmol) in isopropanol (55 mL) was charged with ethyl bromopyruvate (2.5 mL 20 mmol) and then heated at 95° C. After 17 h the reaction mixture was allowed to cool to ambient temperature, filtered and the solids rinsed with EtOAc. The combined filtrates were concentrated under reduced pressure and purified by chromatography (silica, EtOAc/Hex, 15:85 to 65:35) to give the title compound (3.3 g, 67%) as a tacky yellow solid, which was used in the next step without further purification. 1H-NMR (DCM-d2): δ 7.60 (s, 1H), 7.49-7.59 (m, 3H), 6.89 (d, 1H), 6.56 (d, 1H), 4.37 (q, 2H), 1.38 (t, 3H).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. washthe solids rinsed with EtOAc
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. custompurified by chromatography (silica, EtOAc/Hex, 15:85 to 65:35)

Sources & evidence

ORD record
ord-88232b3cf8bd4ac2981cd214ff841eb6
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

Loading…