Reaction #1563935

ord-56f9c4daa91c44b3b68ba6cd366eaa65

Reaction equation

CC(C)(C)OC(=O)Nc1ccncc1F
tert-butyl (3-fluoropyridin-4-yl)carbamate
NOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]
O-(2,4-dinitrophenyl)hydroxylamine
→
CC(C)(C)OC(=O)Nc1cc[n+](N)cc1F.O=[N+]([O-])c1ccc([O-])c([N+](=O)[O-])c1
1-amino-4-((tert-butoxycarbonyl)amino)-3-fluoropyridin-1-ium 2,4-dinitrophenolate

Reactants

CC(C)(C)OC(=O)Nc1ccncc1F
tert-butyl (3-fluoropyridin-4-yl)carbamate
NOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]
O-(2,4-dinitrophenyl)hydroxylamine

Reagents

None

Solvents

CC#N
MeCN
CC#N
MeCN

Conditions

Temperature
40°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherreaction mass
  2. 2
    Otherreaction mass
  3. 3
    Concentrationwas concentrated at temperature below 40° C. under reduced pressure
  4. 4
    Otherto afford Int-11 (50 g) which
  5. 5
    Otherwas used in the next step without further purification

Procedure

A solution of tert-butyl (3-fluoropyridin-4-yl)carbamate (25.0 g, 125 mmol) in MeCN (200 ml), was added O-(2,4-dinitrophenyl)hydroxylamine (26.64 g, 125 mmol) in MeCN (200 ml), drop wise over 30 min at RT, reaction mass was stirred at 40° C. for 12 hrs, reaction mass was concentrated at temperature below 40° C. under reduced pressure to afford Int-11 (50 g) which was used in the next step without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09402833B2uspto-grants-2016_08