Bromine → HCID 68285248, compound

HRID 1518732Notes

Reaction equation

[Br:1]Br.C([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:21]([CH3:22])=[CH:20][S:19][C:18]=2[C:23]([O:25][CH3:26])=[O:24])=[CH:13][C:12]=1[CH3:27])(=[O:10])=[O:9])(C)(C)C>C(Cl)Cl>[Br:1][C:20]1[S:19][C:18]([C:23]([O:25][CH3:26])=[O:24])=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([S:8](=[O:10])(=[O:9])[NH2:7])=[C:12]([CH3:27])[CH:13]=2)[C:21]=1[CH3:22]

Participants

Conditions

Temperature: 25 °C

Procedure

Bromine (0.35 g, 0.11 ml, 2.2 mmol) was added drop wise to a stirred suspension of methyl 3-(4-(N-(tert-butyl)sulfamoyl)-3-methylphenyl)-4-methylthiophene-2-carboxylate (41a, 0.70 g, 1.83 mmol) in DCM (15 ml) at 0° C. The reaction mixture was then stirred at 25° C. for 3 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated. DCM (50 ml) was added to the residue. The mixture so obtained was washed with water (2×20 ml), brine (lx 20 ml) and dried over sodium sulfate. The dried organic layer was then concentrated under reduced pressure to obtain a crude product as semi-solid (0.7 g), which was then purified by flash column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.63 g, 85.13%).

Workup

concentrationThe reaction mixture was then concentrated
additionDCM (50 ml) was added to the residue
customThe mixture so obtained
washwas washed with water (2×20 ml), brine (lx 20 ml)
dry with materialdried over sodium sulfate
concentrationThe dried organic layer was then concentrated under reduced pressure
customto obtain a crude product as semi-solid (0.7 g), which
customwas then purified by flash column chromatography

Sources & evidence

ORD record: ord-ff12182ed958486dba0598c5bee511b5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09072731B2

Reaction notes

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