[NH:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[NH2:13][C:14]1[C:19]([S:20](Cl)(=[O:22])=[O:21])=[CH:18][C:17]([Br:24])=[CH:16][N:15]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[NH2:13][C:14]1[C:19]([S:20]([N:1]2[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]2)(=[O:22])=[O:21])=[CH:18][C:17]([Br:24])=[CH:16][N:15]=1
To a solution of (R)-pyrrolidin-3-ol (32 mg, 0.37 mmol) and potassium carbonate (102 mg, 0.74 mmol) in dioxane (2 mL) and water (400 uL) was added 2-amino-5-bromopyridine-3-sulfonyl chloride (100 mg, 0.37 mmol, prepared according to the methods in WO2008144463). The reaction mixture was stirred for 2 h at rt. Saturated sodium bicarbonate was then added, and the aqueous solution was extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide (R)-1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ol (87.3 mg, 0.27 mmol, 73% yield) as a white solid. 1H NMR (400 MHz, DMSO-D6-d6) δ 8.31 (d, 1H), 7.92 (d, 1H), 6.85 (br s, 2H), 5.02 (br s, 1H), 4.23 (dt, 1H), 3.38-3.25 (m, 3H), 3.14-3.06 (m, 1H), 1.92-1.81 (m, 1H), 1.77-1.67 (m, 1H); MS (EI) for C9H12BrN3O3S: 322, 324 (Br isotopes, MH+).
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