Ethyl bromoacetate → HCID 89768092, compound

HRID 591551Notes

Reaction equation

HRID 591551 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]2[CH:10]([NH2:13])[CH2:11][O:12][C:8]=2[CH:7]=1.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]2[CH:10]([NH:13][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:11][O:12][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 63097602HCID 63097602, compound

Product 1

HCID 89768092HCID 89768092, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-amine (127.3 mg) and THF (4.0 mL) were added TEA (0.172 mL) and ethyl 2-bromoacetate (0.055 mL) at 0° C. The mixture was stirred at room temperature for 4 h. The mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (32.0 mg).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-5b09640c78164201900393d9c7e1b064
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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