Ethyl bromopyruvate → HCID 59251254, compound

HRID 1466418Notes

Reaction equation

HRID 1466418 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[NH:7])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:25][C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>CCO>[CH2:30]([O:29][C:27]([C:26]1[N:7]=[C:6]([C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][CH:4]=2)[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:25]=1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178512096HCID 178512096, compound

Product 1

HCID 59251254HCID 59251254, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 4-bromo-N-(2-chlorobenzyl)-benzamidine (1.4 g, 4.3 mmol), sodium bicarbonate (0.72 g, 8.6 mmol) and ethyl bromopyruvate (0.98 mL, 7.8 mmol) in EtOH (14 mL) was heated in a microwave unit (Biotage Initiator™) at 175° C. for 12 min. The resulting mixture was decanted and the solids rinsed with EtOAc. The combined filtrates were concentrated and purified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60) to give the title compound (0.24 g, 13%) as a pale brown residue. 1H-NMR (DCM-d2): 0.5-7.58-7.62 (m, 3H), 7.43-7.49 (m, 3H), 7.34 (m, 1H), 7.28 (m, 1H), 6.96 (d, 1H), 5.30 (s, 2H), 4.32 (q, 2H), 1.35 (t, 3H); MS (ES): 419, 421 [M+H]+.

Workup

  1. customThe resulting mixture was decanted
  2. washthe solids rinsed with EtOAc
  3. concentrationThe combined filtrates were concentrated
  4. custompurified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60)

Sources & evidence

ORD record
ord-30660b1897f7424f8640ab9ed820748f
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

Loading…