Tetrahydrofuran → N-(2-Bromo-5-iodopyridin-4-yl)methanesulfonamide

HRID 2205854Notes

Reaction equation

HRID 2205854 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N:8](S(C)(=O)=O)[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([I:17])=[CH:4][N:3]=1.C1COCC1.[OH-].[Na+]>O>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([I:17])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86706268N-(2-Bromo-5-iodopyridin-4-yl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 86706267N-(2-Bromo-5-iodopyridin-4-yl)methanesulfonamideYield 84.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(2-Bromo-5-iodopyridin-4-yl)-N-(methylsulfonyl)methanesulfonamide (7) (228 mg, 0.50 mmol) was stirred with THF (1.3 ml) and 10% sodium hydroxide in water (1.3 mL) at r.t. for 3 hours. The THF was evaporated and the aqueous was neutralised using 10% citric acid solution. The deposited white solid was filtered off and washed with water, then dried in a vacuum desiccator over sodium hydroxide to give the title compound (159 mg 84%). 1H-NMR (d6-DMSO, 500 MHz): δ 3.29 (s, 3H), 7.54 (s, 1H), 8.64 (s, 1H)

Workup

  1. customThe THF was evaporated
  2. filtrationThe deposited white solid was filtered off
  3. washwashed with water
  4. dry with materialdried in a vacuum desiccator over sodium hydroxide

Sources & evidence

ORD record
ord-2a4e3d9802964f0f8c2515d95753501a
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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