Potassium Carbonate → (R)-1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-ol

HRID 241042Notes

Reaction equation

HRID 241042 reaction equation
[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

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2759337(R)-3-PyrrolidinolHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 66820212(R)-1-(2-amino-5-bromopyridin-3-ylsulfonyl)pyrrolidin-3-olYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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+).

Workup

  1. customprepared
  2. extractionthe aqueous solution was extracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb968e8e42c54d8f902e16e53f228084
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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