Trimethylsilyldiazomethane → Methyl 6-amino-3-bromopyridine-2-carboxylate

HRID 336605Notes

Reaction equation

HRID 336605 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([Br:11])=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:13]>C(OCC)(=O)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:13])=[O:9])[C:5]([Br:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 467388136-Amino-3-bromopyridine-2-carboxylic acid

Product 1

HCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-amino-3-bromopicolinic acid (30 g) in ethyl acetate (300 mL) and methanol (300 mL) was added TMS-diazomethane (70 mL, 2M in hexanes) and the reaction mixture was stirred for 3 days. The mixture was concentrated, taken up in ether (500 mL) and washed with aqueous Na2CO3 solution (twice), then washed with brine, dried over sodium sulfate, filtered and concentrated to provide the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with aqueous Na2CO3 solution (twice),
  3. washthen washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61c86a1efd6d491cb8057cbac6bf5b47
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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