N-bromobutanimide → 4-Bromo-7-methoxy-2-methylfuro[2,3-c]pyridine

HRID 518486Notes

Reaction equation

HRID 518486 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:11]=[C:10]([CH3:12])[O:9][C:8]=12.C1C(=O)N([Br:20])C(=O)C1>C(#N)C>[Br:20][C:6]1[CH:5]=[N:4][C:3]([O:2][CH3:1])=[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 586224667-Methoxy-2-methylfuro[2,3-c]pyridine

Product 1

HCID 1180214804-Bromo-7-methoxy-2-methylfuro[2,3-c]pyridineYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-methoxy-2-methylfuro[2,3-c]pyridine (3.2 g, 19.6 mmol) in ACN (30 mL) was treated with NBS (3.5 g, 19.7 mmol). After the mixture was stirred at rt for 18 h, it was concentrated in vacuo and purified by silica gel chromatography (PE/EA=30:1˜5:1) to afford the title compound (3.0 g, 64%) as a yellow solid. LCMS (M+H)+=243.

Workup

  1. concentrationit was concentrated in vacuo
  2. custompurified by silica gel chromatography (PE/EA=30:1˜5:1)

Sources & evidence

ORD record
ord-88aa4081bd144f83bd56cd999a9cdb3f
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

Loading…