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

HRID 575756Notes

Reaction equation

HRID 575756 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-9d9f37484c124535985d503359c7995a
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

Loading…