Ethyl bromoacetate → ethyl 2-(7-bromo-3-chloro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate

HRID 931598Notes

Reaction equation

HRID 931598 reaction equation
BrBr.Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:10][C:11]1[CH:12]=[C:13]2[C:23](=[CH:24][CH:25]=1)[O:22][C:16]1[CH:17]=[N:18][C:19]([Cl:21])=[CH:20][C:15]=1[C:14]2=[O:26].C1COCC1>C(OCC)C.[Zn]>[Br:10][C:11]1[CH:12]=[C:13]2[C:23](=[CH:24][CH:25]=1)[O:22][C:16]1[CH:17]=[N:18][C:19]([Cl:21])=[CH:20][C:15]=1[C:14]2([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[OH:26]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24408BromineHCID 574756367-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one

Product 1

HCID 86658372ethyl 2-(7-bromo-3-chloro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetateYield 97.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

Bromine (0.072 ml, 1.4 mmol) was added to a suspension of zinc dust (1.41 g, 21.57 mmol) in diethyl ether (25 ml) at RT. After 5 minutes, ethyl 2-bromoacetate (1.202 ml, 10.8 mmol) was added drop wise over a time period of 10 minutes and the reaction mixture was heated to reflux for 2 hours. 7-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one (2 g, 6.44 mmol) was added in one portion, followed by THF (25.00 ml) and the reaction mixture was heated to reflux for 30 minutes. The reaction mixture was quenched with aqueous saturated NH4Cl solution (20 mL) and water (20 mL) and stirred 30 min at RT. The solution was filtered and the organic phase was separated. The solvent was removed under educed pressure to afford ethyl 2-(7-bromo-3-chloro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate (2.5 g, 6.27 mmol, 97% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 30 minutes
  5. customThe reaction mixture was quenched with aqueous saturated NH4Cl solution (20 mL) and water (20 mL)
  6. filtrationThe solution was filtered
  7. customthe organic phase was separated
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-1252cae9ef9d4f808e6ef2a14acc4c80
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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