Methanesulfonyl chloride → HCID 57545815, compound

HRID 445630Notes

Reaction equation

HRID 445630 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:11]([CH3:10])(=[O:13])=[O:12])[C:5]([CH3:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 219640965-Bromo-2-methylpyridin-3-amine

Product 1

HCID 57545815HCID 57545815, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-bromo-2-methyl-pyridin-3-ylamine (Stage 75.1.4, 573 mg, 3.06 mmol) in pyridine (6 ml) was added dropwise methanesulfonyl chloride (Aldrich, Buchs, Switzerland, 0.286 ml, 3.68 mmol). The reaction mixture was stirred for 18 h at rt then are added methanesulfonyl chloride (0.03 ml, 0.39 mmol). The reaction mixture was stirred 4 h at rt before being evaporated to dryness. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and evaporated. The crude product was dry loaded on silica gel and purified by MPLC (DCM/MeOH 0%-5%) to give the title compound as a pinkish solid. (HPLC: tR 2.05 min (Method A); M+H=265, 267 MS-ES).

Workup

  1. stirringThe reaction mixture was stirred 4 h at rt
  2. custombefore being evaporated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. dry with materialThe crude product was dry
  9. custompurified by MPLC (DCM/MeOH 0%-5%)

Sources & evidence

ORD record
ord-be7f44a185944d26b70e0eaa1e13a9b7
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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