Pyridine → 6-Bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine

HRID 1770823Notes

Reaction equation

HRID 1770823 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Br:10])[N:3]=1.N1C=CC=CC=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[Br:10][C:4]1[N:3]=[C:2]([NH:1][C:17]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[C:7]([O:8][CH3:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 575629062-Amino-6-bromo-3-methoxypyridine

Product 1

HCID 575628846-Bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A dry reaction flask equipped with a nitrogen inlet and magnetic stirring bar was charged with 2-amino-6-bromo-3-methoxypyridine (33) (0.170 g, 0.84 mmol), pyridine (0.126 mL, 1.26 mmol) and CH2Cl2 (5 mL). To this at 0° C. was added pivaloyl chloride (0.113 mL, 0.92 mmol) and then the reaction mixture was stirred at room temperature overnight. The reaction was then quenched with water (25 mL), extracted with CH2Cl2 (2×25 mL), dried over anhydrous sodium sulfate and solvent was removed under reduced pressure to afford 6-bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine (34). LCMS: purity: 80%; MS (m/z): 287 (MH+).

Workup

  1. customA dry reaction flask
  2. customequipped with a nitrogen inlet and magnetic stirring bar
  3. customThe reaction was then quenched with water (25 mL)
  4. extractionextracted with CH2Cl2 (2×25 mL)
  5. dry with materialdried over anhydrous sodium sulfate and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-c65cf7d72d55458581cfa4b08903f27a
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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