Methanol → 7-Bromofuro[3,2-c]pyridin-4(5H)-one

HRID 910073Notes

Reaction equation

HRID 910073 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]1[C:17]2[CH:16]=[CH:15][NH:14][C:13](=[O:18])[C:12]=2[CH:11]=[CH:10]1.CO>C(#N)C>[Br:1][C:16]1[C:17]2[O:9][CH:10]=[CH:11][C:12]=2[C:13](=[O:18])[NH:14][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 67184N-bromobutanimideHCID 2887464H,5H-furo(3,2-c)pyridin-4-one

Product 1

HCID 179855277-Bromofuro[3,2-c]pyridin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Add N-bromosuccinimide (63.16 g, 354.9 mmol) as a solution in anhydrous acetonitrile (480 mL) to a suspension of 5H-furo[3,2-c]pyridin-4-one (36.9 g, 273 mmol) in anhydrous acetonitrile (740 mL) at 0° C. over 1 hour. Warm to room temperature, add anhydrous methyl alcohol (1.5 L) and stir at room temperature for 18 hours. Quench with water (20 ml) and saturated sodium bicarbonate (20 mL), concentrate to a volume of 1.3 liters, and pour into water (1.3 L). Collection of the precipitate by filtration and drying (vacuum oven 2 days 40-60° C.) gives the title compound as an off-white solid.

Workup

  1. customQuench with water (20 ml) and saturated sodium bicarbonate (20 mL)
  2. concentrationconcentrate to a volume of 1.3 liters
  3. additionpour into water (1.3 L)
  4. customCollection of the precipitate
  5. filtrationby filtration
  6. customdrying (vacuum oven 2 days 40-60° C.)

Sources & evidence

ORD record
ord-b2e55d8903884003935eaf7d591828c2
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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