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

HRID 1661662Notes

Reaction equation

HRID 1661662 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-d5943d16259947249d5127be81e10437
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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