Water → 4-Bromo-5-(cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamide

HRID 1844739Notes

Reaction equation

C1C(=O)N([Br:8])C(=O)C1.[CH:9]1([CH2:15][C:16]2[N:20]([CH3:21])[C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O>C1COCC1>[Br:8][C:17]1[CH:18]=[C:19]([S:22]([NH2:25])(=[O:24])=[O:23])[N:20]([CH3:21])[C:16]=1[CH2:15][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of NBS (68.7 mg, 386 μmol) was added a solution of compound 25e (104 mg, 410 μmol) in THF at −78° C. and stirred for 2 h at −78° C. Water (30 mL) was added and the reaction mixture was extracted with EA (150 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by CC (hexane/EA=3/1) to give compound 25f (134 mg, 61%).

Workup

extractionthe reaction mixture was extracted with EA (150 mL)
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified by CC (hexane/EA=3/1)

Sources & evidence

ORD record: ord-5e4988c72fec42c39b0f3099d8f825d1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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