HCID 66820425, compound → HCID 66820532, compound

HRID 241054Notes

Reaction equation

HRID 241054 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:16][C:4]1[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 1

HCID 66820425HCID 66820425, compound

Product 1

HCID 66820532HCID 66820532, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Iron powder (293 mg, 5.2 mmol) was added to a solution of tert-butyl 5-bromo-3-nitropyridin-2-ylcarbamate (167 mg, 0.52 mmol) in acetic acid (2.5 mL). The mixture was stirred at 60° C. for 1 h 20 min before cooling to rt. The mixture was then diluted with ethyl acetate, and solids were removed by filtration through celite. The filtrate was washed with water followed by saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo to provide tert-butyl 3-amino-5-bromopyridin-2-ylcarbamate (96.3 mg, 0.33 mmol, 64% yield) as a gray solid. 1H NMR (400 MHz, CDCl3) δ 7.83 (d, 1H), 7.20 (d, 1H), 6.95 (br s, 1H), 4.42 (br s, 2H), 1.51 (s, 9H); MS (EI) for C10H14BrN3O2: 232, 234 (Br isotopes, MH+-t-butyl).

Workup

  1. temperaturebefore cooling to rt
  2. customwere removed by filtration through celite
  3. washThe filtrate was washed with water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-067dc7d89ff046c39893c329810d9e3d
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…