Acetic Acid → N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

HRID 1623507Notes

Reaction equation

HRID 1623507 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[CH2:10]([S:12]([NH2:15])(=[O:14])=[O:13])[CH3:11].C(O)(=O)C.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:15][S:12]([CH2:10][CH3:11])(=[O:14])=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 73702EthanesulfonamideHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-bromo-3-pyridinecarboxaldehyde (CAS#113118-81-3, 450 mg, 2.4 mmol) in dichloroethane (15 mL) was added ethanesulfonamide (CAS#1520-70-3, 175 mg, 1.6 mmol), acetic acid (0.18 mL 3.2 mmol), triethylamine (0.45 mL, 3.2 mmol) and sodium triacetoxyborohydride (1.0 g, 4.8 mmol). The reaction was stirred at room temperature for 3 hours, at which time it was diluted with dichloromethane and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide; MS: (ES+) m/z 278.9 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted two additional times with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%)

Sources & evidence

ORD record
ord-a2c6bc8e33c3408b967f400b2f7cc583
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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