Methyl chloroformate → Methyl (5-bromopyridin-2-yl)carbamate

HRID 611618Notes

Reaction equation

HRID 611618 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:19]([O:21][CH3:22])=[O:20]>C(Cl)(Cl)Cl>[CH3:22][O:21][C:19](=[O:20])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 706222-Amino-5-bromopyridineHCID 81531Diisopropylethylamine

Product 1

HCID 790797Methyl (5-bromopyridin-2-yl)carbamateYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-5-bromopyridine (9.46 g, 20 mmol) and N,N-diisopropylethylamine (3.10 g) in chloroform (20 ml) was added to a solution of methyl chloroformate (2.30 g, 24 mmol) in chloroform (25 ml) dropwise with stirring at 0° C. The reaction mixture was stirred for 20 minutes, filtered and the precipitate was washed with chloroform and dried to afford 1.71 g (37%) of the title product as a white solid. mp 191-192° C. 1H NMR (CDCl3): δ=8.42 (d, 1 H); 8.30 (d, 1 H); 7.91 (d, 1 H); 7.77 (d of d, 1 H); 3.79 (s, 3 H). MS (El): m/z=230, 232 (M+, Br isotopes).

Workup

  1. stirringThe reaction mixture was stirred for 20 minutes
  2. filtrationfiltered
  3. washthe precipitate was washed with chloroform
  4. customdried

Sources & evidence

ORD record
ord-4a6fe7aff47b4c51a876b153eaf40386
Source dataset
uspto-grants-1999_12
Patent number
US06001856

Reaction notes

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