3-Pyridinemethanamine → HCID 25235487, compound

HRID 1948989Notes

Reaction equation

HRID 1948989 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:6]=[CH:5]2.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH2:29])[CH:23]=1>O1CCOCC1>[O:15]([CH2:14][CH2:13][NH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:29][CH2:28][C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)[CH:3]=2)[N:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 685743166-Chloro-N-(2-phenoxyethyl)-2-quinolinamine

Product 1

HCID 25235487HCID 25235487, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

(6-Chloro-quinolin-2-yl)-(2-phenoxy-ethyl)-amine (150 mg, 0.503 mmol) was dissolved in 2 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 3-Picolylamine (165 mg, 1.53 mmol), sodium tert.-butylate (119 mg, 1.24 mmol) and 1,1′-2-(dimethylamino)ferrocen-1-yl-palladium(II) chloride dinorbornylphosphine (16 mg, 0.03 mmol) were added. The reaction mixture was stirred in a sealed tube at 115° C. for 16 h. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient). The title compound was obtained as a light brown solid (108 mg, 58%), MS: m/e=371.1 (M+H+).

Workup

  1. customArgon was bubbled through the solution for 2 minutes
  2. customto remove oxygen
  3. customThe solvent was evaporated
  4. customthe residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record
ord-262b4592eb2b407f8e1e7e65b0202d77
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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