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

HRID 557172

Reaction equation

HRID 557172 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-9bd1f2e713f14c15b1a56ea1de3a101f
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Linked notes

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