N-bromobutanimide → HCID 86608778, compound

HRID 2387624Notes

Reaction equation

[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]([C:12]2[S:13][CH:14]=[N:15][N:16]=2)[N:10]=[C:9]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[S:8]1)=[N+:2]=[N-:3].[Br:31]N1C(=O)CCC1=O>C(#N)C>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]([C:12]2[S:13][C:14]([Br:31])=[N:15][N:16]=2)[N:10]=[C:9]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[S:8]1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 60 °C

Procedure

2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-1,3,4-thiadiazole (0.020 g, 0.0451 mmol) was dissolved in 0.25 mL ACN, followed by addition of N-Bromosuccinimide (0.00883 g, 0.0496 mmol), and the reaction mixture was heated at 60° C. for 14 hours. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was then purified by flash column chromatography, eluting with 5.3:1 (hexanes/ethyl acetate), to afford the desired product as a thick golden oil (22 mg, 93%).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was then purified by flash column chromatography
washeluting with 5.3:1 (hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-9c682d5c4ff941c582917e126dc39a1d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268871B2

Reaction notes

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