Phenacyl bromide → HCID 53310698, compound

HRID 2389922Notes

Reaction equation

HRID 2389922 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:15]1([C:13]2[N:10]=[C:6]3[CH:7]=[CH:8][C:9]4[O:1][CH2:2][CH2:3][C:4]=4[N:5]3[CH:12]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 552820545-Amino-2,3-dihydrofuro[3,2-b]pyridine

Product 1

HCID 53310698HCID 53310698, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,3-dihydrofuro[3,2-b]pyridin-5-amine (500 mg, 3.67 mmol) in ethanol (30 mL) were added 2-bromo-1-phenylethanone (730 mg, 3.67 mmol) and sodium carbonate (467 mg, 4.40 mmol), and the mixture was stirred at 80° C. for 14 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→50/50) to give the title compound (136 mg, yield 16%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→50/50)

Sources & evidence

ORD record
ord-e383beb73d9f44339c4836697b2fe576
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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