Water → 5-Bromo-1-(cyclohexylmethyl)-N-cyclopropyl-2-methyl-1H-pyrrole-3-sulfonamide

HRID 1844710Notes

Reaction equation

[CH:1]1([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH:17]3[CH2:19][CH2:18]3)(=[O:15])=[O:14])=[C:9]2[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:28])C(=O)C1.O>C1COCC1>[Br:28][C:12]1[N:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:9]([CH3:20])=[C:10]([S:13]([NH:16][CH:17]2[CH2:19][CH2:18]2)(=[O:15])=[O:14])[CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of compound 3c (3.0 g, 10.0 mmol) in THF (80 mL) at −78° C. was added a solution of NBS (1.78 g, 10.0 mmol) in THF (50 mL) and the solution was stirred for 2 h at −78° C. Water was added and the solution was extracted with EA twice. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified CC (EA/PE=1/5) to give compound 3d (3.2 g, 85%) as a white solid.

Workup

extractionthe solution was extracted with EA twice
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified CC (EA/PE=1/5)

Sources & evidence

ORD record: ord-f9fccbfabcd24cb8ae8ce87bb4e8da21
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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