Sodium Carbonate → (3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone

HRID 81474

Reaction equation

HRID 81474 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[Na+].[Na+].[Br:22]Br>C(O)(=O)C>[NH2:1][C:2]1[C:3]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[N:4][C:5]([Br:22])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 24408Bromine2×HCID 68630652(3-Amino-pyrazin-2-yl)-pyridin-3-yl-methanone

Product 1

HCID 86634541(3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

(3-Amino-pyrazin-2-yl)-pyridin-3-yl-methanone (1.00 g, 4.99 mmol) is dissolved in glacial acetic acid (10 ml). Na2CO3 (0.583 g, 5.49 mmol) is added. After evolution of gas has finished, a solution of bromine (0.192 ml, 3.74 mmol) in acetic acid (5 ml) is added dropwise. Na2CO3 (0.583 mg, 5.49 mmol) is added, followed by a second solution of bromine (0.192 ml, 3.74 mmol) in acetic acid (5 ml). The resulting orange suspension is left to stir for 1 hour. The reaction is quenched by pouring onto ice water (150 ml), and the orange solid formed is collected by filtration, washed with water and dried in vacuo at 40° C. overnight to yield the title compound. [M+H]+ 279.

Workup

  1. waitThe resulting orange suspension is left
  2. customThe reaction is quenched
  3. additionby pouring onto ice water (150 ml)
  4. customthe orange solid formed
  5. filtrationis collected by filtration
  6. washwashed with water
  7. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-2df8dadc6d6444069182564d5bc89b78
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Linked notes

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