Pyridine → HCID 86623896, compound

HRID 1666366Notes

Reaction equation

HRID 1666366 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:22](=[O:23])[O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 6428116-Bromopyridin-3-amine

Product 1

HCID 86623896HCID 86623896, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-5-aminopyridine (3.0 g, 17.3 mmol) in THF (44 mL) cooled to 0° C. was added pyridine (1.8 mL, 21.7 mmol) followed by phenylchloroformate (2.3 mL, 18.2 mmol). A precipitate formed and the reaction was stirred at 0° C. for 1 h. The reaction was stirred at RT overnight and quenched with 1N HCl. The mixture was extracted with EtOAc. The organic layer was washed with water, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated to give the title compound as a biege solid (4.81 g, 94% yield).

Workup

  1. customA precipitate formed
  2. stirringThe reaction was stirred at RT overnight
  3. customquenched with 1N HCl
  4. extractionThe mixture was extracted with EtOAc
  5. washThe organic layer was washed with water, saturated aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b8592a03e6fd48e78db0245ac0172ee1
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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