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

HRID 911943Notes

Reaction equation

[O:1]1[C:9]2[CH:8]=[CH:7][NH:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:18])C(=O)C1.O.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:18][C:8]1[C:9]2[O:1][CH:2]=[CH:3][C:4]=2[C:5](=[O:10])[NH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 5H-furo[3,2-c]pyridin-4-one (11.1 g, 0.082 mol) in anhydrous acetonitrile (200 mL) was added a solution of NBS (19.0 g, 0.107 mol) in anhydrous acetonitrile (100 ml) at 0° C. over 1 h. The resulting suspension was stirred at 0° C. for 1 h and then warmed to rt for 10 min. Water (500 mL) and saturated sodium bicarbonate aqueous solution (4 ml) were added to the mixture. Off-white solids were collected by filtration and dried under vacuum to afford 7.33 g of desired product (yield: 42%). 1H NMR (DMSO-d6, 400 MHz): δ=7.06 (d, J=2.3 Hz, 1H), 7.60 (s, 1H), 8.00 (d, J=2.0 Hz, 1H). MS (ES+): 214.04/216.04 (1/1) [MH+].

Workup

temperaturewarmed to rt for 10 min
filtrationOff-white solids were collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-564f9c4d803b4c3b9f98bf80be9aba86
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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