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

HRID 1778903Notes

Reaction equation

HRID 1778903 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 saturated Na2CO3 solution (twice) and brine, then dried over sodium sulfate, filtered and concentrated to provide the title compound.

Workup

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

Sources & evidence

ORD record
ord-f52d48cffd074ff7a8eeb047759bd4fd
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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