Einecs 211-027-4 → 5-Amino-3-methyl-9H-pyrido[2,3-b]indole-7-carbonitrile

HRID 1642540Notes

Reaction equation

HRID 1642540 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH2:18])[C:9]=1[C:10]1[C:11](F)=[N:12][CH:13]=[C:14]([CH3:16])[CH:15]=1)[C:5]#[N:6].[Cl-].[NH+]1C=CC=CC=1>O1CCOCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[C:8]2[C:9]=1[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[N:12][C:11]=1[NH:18]2

Participants

4

Reactant 2

HCID 69401Einecs 211-027-4HCID 588800563,5-Diamino-4-(2-fluoro-5-methyl-pyridin-3-yl)-benzonitrile

Product 1

HCID 161243115-Amino-3-methyl-9H-pyrido[2,3-b]indole-7-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

Compound 123 (148 mg, 0.61 mmol) was dissolved in dioxane (2 mL) with pyridinium chloride (80 mg), and the solution was heated at 180° C. in the microwave for 15 minutes. The solution was concentrated in vacuo. Purification by flash chromatography (20% acetone/CH2Cl2) gave 118 mg (87%) of the title compound as an off-white solid. MS (ES) [m+H] calc'd for C13H10N4, 223; found 223.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customPurification by flash chromatography (20% acetone/CH2Cl2)

Sources & evidence

ORD record
ord-2ce6133bc03f49c5a63b0fbe41f72d8b
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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