Triethylamine → 5-bromo-N-(3-pyridinylmethyl)-2-thiophenesulfonamide

HRID 558535Notes

Reaction equation

HRID 558535 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[Br:9][C:10]1[S:14][C:13]([S:15](Cl)(=[O:17])=[O:16])=[CH:12][CH:11]=1.C(N(CC)CC)C>C1COCC1>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][S:15]([C:13]2[S:14][C:10]([Br:9])=[CH:11][CH:12]=2)(=[O:17])=[O:16])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 6626665-bromo-N-(3-pyridinylmethyl)-2-thiophenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-aminomethyl-pyridine (1.24 g, 11.5 mmol) in THF (8 ml) was added at 0° C. (ice water bath) commercially available 5-bromo-thiophene-2-sulfonyl chloride (1.0 g, 3.82 mmol) dissolved in THF (8 ml) and triethylamine (0.59 ml, 4.21 mmol). The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by flash chromatography (dichloromethane/methanol) and crystallization from dichloromethane/hexane to yield the title compound (1.23 g, 97%) as a white solid. MS (ISN) 331.0 [(M−H)−], mp 125° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography (dichloromethane/methanol) and crystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-76d9812f694a41ac965ac7647d827b04
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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