Methanesulfonyl chloride → N-(5-Bromo-pyridin-2-ylmethyl)-N-methoxy-methane sulfonamide

HRID 525538Notes

Reaction equation

HRID 525538 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][O:10][CH3:11])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>O1CCCC1.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([O:10][CH3:11])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 78955627N-(5-Bromo-pyridin-2-ylmethyl)-O-methyl-hydroxylamine

Product 1

HCID 86695426N-(5-Bromo-pyridin-2-ylmethyl)-N-methoxy-methane sulfonamideYield 36.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of N-(5-Bromo-pyridin-2-ylmethyl)-O-methyl-hydroxylamine (0.6 g, 2.765 mmol) in tetrahydrofuran (10 mL) is added sodium bis(trimethylsilyl)-amide (0.6 g, 3.318 mmol) and mesyl chloride (0.37 g, 3.318 mmol) at 0° C. The reaction mixture is stirred at room temperature for 16 hours. Reaction mixture diluted with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by flash chromatography using 20% ethyl acetate in hexane as an eluent to afford the title compound (0.3 g). 1HNMR (400 MHz, DMSO-d6) δ: 3.14 (s, 3H), 3.47 (s, 3H), 4.40 (s, 2H), 7.50 (d, J=8.28 Hz, 1H), 8.09-8.12 (dd, J1=2.8 Hz, J2=8.4 Hz, 1H), 8.71 (d, J=2.36 Hz, 1H). LC-MS (m/z): [M+H]=297.1.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1703cd31fc264c5d9ecf06eada787ff2
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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