Potassium Cyanide → Methyl 6-[(5-cyano-2-pyridinyl)oxy]-9H-pyrido[3,4-b]indole-3-carboxylate

HRID 1087868Notes

Reaction equation

HRID 1087868 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18][C:19]1[CH:24]=[CH:23][C:22](N)=[CH:21][N:20]=1)=[CH:12][CH:11]=3)=[O:4].N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cu][C:37]#[N:38].[C-]#N.[K+]>O.Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:37]#[N:38])=[CH:21][N:20]=1)=[CH:12][CH:11]=3)=[O:4]

Participants

8

Reactant 5

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 54171784HCID 54171784, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 14071992Methyl 6-[(5-cyano-2-pyridinyl)oxy]-9H-pyrido[3,4-b]indole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A suspension of 1.7 g of amino derivative (Example 24) in 10 ml of water and 2.5 ml of hydrochloric acid (37%) is combined dropwise at -5° C. with a solution of 0.4 g of NaNO2 in 1.5 ml of water, then stirred for another hour at 0°-5° C. By adding sodium carbonate, the solution is then adjusted to pH 5.5-6 and poured into a mixture, preheated to about 60° C., of 0.5 g of copper (I) cyanide and 1.6 g of potassium cyanide in 10 ml of water. After the reaction is completed, the cooled-off solution is extracted with dichloromethane, the organic phase is washed with water and concentrated. The residue is purified over silica gel, thus obtaining 1.12 g (65%).

Workup

  1. additionpoured into a mixture
  2. extractionthe cooled-off solution is extracted with dichloromethane
  3. washthe organic phase is washed with water
  4. concentrationconcentrated
  5. customThe residue is purified over silica gel
  6. customthus obtaining 1.12 g (65%)

Sources & evidence

ORD record
ord-43220338c2864bbf9c01bd8d1be1cb29
Source dataset
uspto-grants-1990_10
Patent number
US04960777

Reaction notes

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