Trimethylsilyldiazomethane → Methyl 3,5-dichloropyrazine-2-carboxylate

HRID 1526586Notes

Reaction equation

HRID 1526586 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1.[CH3:12][Si](C=[N+]=[N-])(C)C>CO.C(OCC)C>[Cl:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 226655363,5-Dichloropyrazine-2-carboxylic acid

Product 1

HCID 22665557Methyl 3,5-dichloropyrazine-2-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3,5-dichloropyrazine-2-carboxylic acid (0.304 g, 1.58 mmol) in MeOH (5 mL) and diethyl ether (5 mL) at room temperature was added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 4.00 mL, 8.00 mmol). The reaction mixture was stirred at RT for 30 min and concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol, 96% yield) as a white solid. LC/MS

Workup

  1. concentrationconcentrated
  2. customPurification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4538a561bbed438d9cd2d4605465155b
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

Loading…