Ethyl bromoacetate → HCID 56598518, compound

HRID 72653Notes

Reaction equation

HRID 72653 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([CH2:10][S:11](/[CH:14]=[CH:15]/[C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=2[O:26][CH3:27])(=[O:13])=[O:12])=[CH:5][N:4]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:8]([NH:9][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:7][C:6]([CH2:10][S:11](/[CH:14]=[CH:15]/[C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=2[O:26][CH3:27])(=[O:13])=[O:12])=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 56598517HCID 56598517, compound

Product 1

HCID 56598518HCID 56598518, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-amine (28 mg, 0.072 mmol) in DMF (5 mL), ethyl bromoacetate (0.110 mL, 1 mmol) and potassium carbonate (138 mg, 1 mmol) were added. The mixture was stirred at 60° C. overnight. The mixture was diluted with H2O (20 mL) and extracted (2×20 mL ethyl acetate). The combined extracts were washed with brine, dried on MgSO4, and filtered. The residue was further purified by silica gel chromatography, eluting with PE/EtOAc (2:3, v/v) to afford pure product as a white solid (24.2 mg, 70%). 1H-NMR (CDCl3): δ 3.85 (s, 6H, 2×OCH3), 3.87 (s, 3H, OCH3), 3.90 (d, 2H, J=2.8 Hz, CH2), 4.00 (s, 3H, OCH3), 4.15 (s, 2H, CH2), 4.27 (q, 2H, CH2), 6.10 (s, 2H, Ph-H), 6.74 (d, 1H, J=2.0 Hz, Py-H), 7.04 (d, 1H, J=15.6 Hz, CH), 7.44 (d, 1H, J=2.0 Hz, Py-H), 7.811 (d, 1H, J=15.6 Hz, CH); HR-MS (ESI+) m/z: 481.1364 [M+H]+; C22H28N2O8S requires 480.1566,

Workup

  1. extractionextracted (2×20 mL ethyl acetate)
  2. washThe combined extracts were washed with brine
  3. customdried on MgSO4
  4. filtrationfiltered
  5. customThe residue was further purified by silica gel chromatography
  6. washeluting with PE/EtOAc (2:3

Sources & evidence

ORD record
ord-4229ce7af8b948eebfbb22703981b598
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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