Aluminum(III) Chloride → (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-nitro-phenyl)-methanone

HRID 60091Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].[F:15][C:16]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>[N+](C)([O-])=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:18]([C:17]3[CH:21]=[CH:22][CH:23]=[C:24]([N+:25]([O-:27])=[O:26])[C:16]=3[F:15])=[O:19])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

5-Bromo-1H-pyrrolo[2,3-b]pyridine (4, 0.525 g, 2.66 mmol) is combined with aluminum trichloride (2.05 g, 15.4 mmol) and 10 mL of nitromethane. 2-Fluoro-3-nitro-benzoyl chloride (17, 0.521 g, 2.56 mmol) in 5 mL of nitromethane is added and the reaction is heated at 45° C. for 6 hours. The reaction is quenched by slowly adding 5 mL of methanol. The resulting precipitate is collected by filtration and combined with ethyl acetate, water and celite, then stirred for 30 minutes and filtered. The organic layer is isolated and washed with water, then brine, dried over magnesium sulfate, filtered and the filtrate is concentrated under vacuum to provide the desired compound (18, 151 mg). MS (ESI) [M−H+]−=362.4 and 364.4.

Workup

customThe reaction is quenched
additionby slowly adding 5 mL of methanol
filtrationThe resulting precipitate is collected by filtration
filtrationfiltered
customThe organic layer is isolated
washwashed with water
dry with materialbrine, dried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record: ord-70b69aad8fa04a02b18cc1269cc0040d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440969B2

Reaction notes

Loading…