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Home > Encyclopedia > 2-Chloro-3-amino-5-bromopyridine

2-Chloro-3-amino-5-bromopyridine

2-Chloro-3-amino-5-bromopyridine structure

2-Chloro-3-amino-5-bromopyridine 

structure
  • CAS No:

    588729-99-1

  • Formula:

    C5H4BrClN2

  • Chemical Name:

    2-Chloro-3-amino-5-bromopyridine

  • Synonyms:

    5-BROMO-2-CHLORO-3-PYRIDINAMINE;5-BROMO-2-CHLORO-PYRIDIN-3-YLAMINE;5-BROMO-2-CHLOROPYRIDIN-3-AMINE;3-AMINO-5-BROMO-2-CHLOROPYRIDINE;2-Chloro-3-amino-5-bromopyridine;3-Amino-5-bromo-2-chloropyridi;3-Amino-5-Bromo-2-Chloropyrid;6-(4-fluorophenyl)-2-hydroxynicotinonitrile

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

Colorless solid

2-Chloro-3-amino-5-bromopyridine Basic Attributes

207.46

205.924637

-0

2933399090

Characteristics

38.9

1.8

1.8±0.1 g/cm3

129-132℃

296.7°C at 760 mmHg

133.3±25.9 °C

1.648

Safety Information

IRRITANT

2811

3

25-37/38-41-22

26-39-45

Xi,T

Irritant

P261-P280-P301 + P310-P305 + P351 + P338

H301-H315-H318-H335

2-Chloro-3-amino-5-bromopyridine Use and Manufacturing

Step 1: a) 3 -amino-5 -bromo-2-chloropyridineTo a stirred suspension of 5-bromo-2-chloro-3-nitropyridine (20.0 g, 84.2 mMol) in cone. HCl (90 mL) was added SnClTo a stirred suspension of 5-bromo-2-chloro-3-nitropyridine (84.2 mmol) in cone. HCl (90 rtiL) was added SnClTo a solution of 5-bromo-2-chloro-3-nitropyridine (4.24 g, 17.86 mmol) in EtOH (89 ml) was added Tin(II) chloride (16.9 g, 89.0 mmol) at room temperature. The mixture was refluxed for 1 hour, and then cooled to room temperature, filtered through a Celite pad and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was treated with saturated aq. NaHCOIntermediate 3; Preparation of 2-amino-N, N-dimethyl-5-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-3-pyridinesulfonamide ; To a solution of 2-amino-5-bromo-N, N-dimethyl-3-pyridinesulfonamide (7.14 mmol) in 1, 4-dioxane (35 mL) was added 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi-1, 3, 2-dioxaborolane (7.86 mmol), potassium acetate (28.56 mmol) and [1, 1'-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.571 mmol). The reaction mixture was stirred at 100° C. for 18 h. The reaction was concentrated in vacuo, re-dissolved in ethyl acetate (50 mL) and purified on silica using 60percent ethyl acetate/hexanes to yield the title compound as a tan solid (86percent).

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