Acetic Acid → N-[(5-Bromo-3-pyridinyl)methyl]methanesulfonamide

HRID 593617Notes

Reaction equation

HRID 593617 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[CH3:10][S:11]([NH2:14])(=[O:13])=[O:12].C(O)(=O)C.C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:14][S:11]([CH3:10])(=[O:13])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 72879MethanesulfonamideHCID 516892Sodium BicarbonateHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59534656N-[(5-Bromo-3-pyridinyl)methyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-bromo-3-pyridine-carboxaldehyde (1.5 g, 7.9 mmol), methanesulfonamide (0.5 g, 5.3 mmol), acetic acid (0.637 g, 10.6 mmol), triethylamine (1.07 g, 10.6 mmol) in DCE (50 mL) at ambient temperature is added NaBH(OAc)3 (3.14 g, 14.84 mmol). The reaction mixture is stirred overnight. Aqueous NaHCO3 (20 mL) is added and the organic phase is separated. The aqueous phase is extracted with dichloromethane and the combined organic phase is dried over Na2SO4. Concentration affords a residue which is purified by silica gel flash chromatography with a methanol in dichloromethane gradient to afford N-(5-bromo-pyridin-3-ylmethyl)-methanesulfonamide as a solid. MS (ESI) m/z 266.9 (M+H)+.

Workup

  1. customthe organic phase is separated
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. dry with materialthe combined organic phase is dried over Na2SO4
  4. concentrationConcentration
  5. customaffords a residue which
  6. customis purified by silica gel flash chromatography with a methanol in dichloromethane gradient

Sources & evidence

ORD record
ord-367516c6b887449fa0a0313f84b5f494
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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