Pyridine → HCID 86585614, compound

HRID 2303471Notes

Reaction equation

HRID 2303471 reaction equation
[OH:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:10][C:5]=2[O:4][C:3]=1[C:15]#[N:16].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:15]([C:3]1[O:4][C:5]2[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=2[C:2]=1[O:1][S:24]([CH3:23])(=[O:26])=[O:25])#[N:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 18461555HCID 18461555, compound

Product 1

HCID 86585614HCID 86585614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 13 (3.9 g) in CH2Cl2 (200 mL) was treated with pyridine (10 mL), methanesulfonyl chloride (4 mL), and a catalytic amount of dimethylaminopyridine at 0° C., under an N2 atmosphere, for 2 h. The reaction was allowed to warm to ambient temperature overnight. The reaction was partitioned between 1:1 Et2O/hexanes and brine. The organic layer was dried (MgSO4), filtered, and evaporated. The residue was purified by chromatography (silica gel, 1:1 EtOAc/hexanes) giving 1.05 g of methanesulfonic acid 2-cyano-6-methanesulfonyl-benzofuran-3-yl ester 14.

Workup

  1. customThe reaction was partitioned between 1:1 Et2O/hexanes and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (silica gel, 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-3b42a6d3c4e34e54a680706989adb150
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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