3-Pyridinemethanamine → N2-(2-Methoxy-benzyl)-N5-pyridin-3-ylmethyl-quinoline-2,5-diamine

HRID 1170071Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH2:29])[CH:23]=1>O1CCOCC1>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([NH:29][CH2:28][C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 3 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 3-Picolylamine (127 mg, 1.18 mmol), sodium tert.-butylate (144 mg, 1.50 mmol), 1,1′-bis(diphenylphosphin)ferrocen (50 mg, 0.09 mmol) and 1,1′-bis(diphenylphosphin)ferrocen-palladium(II)chloride (24 mg, 0.03 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 2.5 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 (183 mg, 85%), MS: m/e=371.1 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-094fece36f064664992fab5fefb3a337
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825253B2

Reaction notes

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