Methanol → HCID 68630898, compound

HRID 81489Notes

Reaction equation

HRID 81489 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Br:22]Br.CO>C(O)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:6][C:5]([Br:22])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium Carbonate2×HCID 24408Bromine2×HCID 53678495(2-Amino-pyridin-3-yl)-pyridin-3-yl-methanone

Product 1

HCID 68630898HCID 68630898, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

(2-Amino-pyridin-3-yl)-pyridin-3-yl-methanone (0.13 g, 0.65 mmol) is dissolved in glacial acetic acid (6 ml). Na2CO3 (0.075 g, 0.72 mmol) is added. After evolution of gas has finished, a solution of bromine (0.025 ml, 0.49 mmol) in acetic acid (3 ml) is added dropwise. Na2CO3 (0.075 g, 0.72 mmol) is added, followed by a second solution of bromine (0.025 ml, 0.49 mmol) in acetic acid (3 ml). The resulting yellow suspension is left to stir for 2 hour. The reaction is quenched by pouring onto ice water (150 ml), and neutralised using NaHCO3. The product is extracted with EtOAc and dried (MgSO4). Concentration in vacuo affords an oil, which is trituatuted with methanol to yield the title compound [M+H]+ 277.

Workup

  1. waitThe resulting yellow suspension is left
  2. customThe reaction is quenched
  3. additionby pouring onto ice water (150 ml)
  4. extractionThe product is extracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration in vacuo
  7. customaffords an oil, which

Sources & evidence

ORD record
ord-293e709cf8fa47f2bbb48395713b7f61
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

Loading…