1,4-Cyclohexadiene → HCID 67463465, compound

HRID 1777719Notes

Reaction equation

C([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[C:17]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:16]=2)=[CH:11][C:10]=1[Cl:31])C1C=CC=CC=1.C1CC=CCC=1>CCO.[OH-].[OH-].[Pd+2]>[Cl:31][C:10]1[CH:11]=[C:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[C:17]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:16]=2)[CH:13]=[CH:14][C:9]=1[NH2:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To the mixture of 4 and benzyl-[2-chloro-4-(5-morpholin-4-yl-[1,6]naphthyridin-7-yl)-phenyl]-amine (60 mg, 1:1.4, 0.128 mmol, 1 eq) in dry EtOH (3 mL) was added Pd(OH)2 (30 mg, 50% w/w) and 1,4-cyclohexanediene (240 μL, 2.56 mmol, 20 eq) under Ar(g). The mixture was heated at 80° C. overnight. Additional quantities of Pd(OH)2 (30 mg, 50% w/w) and 1,4-cyclohexanediene (240 μL, 2.56 mmol, 20 eq) were then added, and the mixture was again heated at 80° C. overnight. Once cooled down, the reaction mixture was filtered through a short celite pad, and eluted with MeOH (10 mL). The solvent was then removed in vacuo and the residue was further purified by silica gel column chromatography using hexane/EtOAc (1:9-0:1) as eluant to furnish E as a pale yellow solid (11.2 mg, 26%).

Workup

temperaturethe mixture was again heated at 80° C. overnight
temperatureOnce cooled down
filtrationthe reaction mixture was filtered through a short celite pad
washeluted with MeOH (10 mL)
customThe solvent was then removed in vacuo
customthe residue was further purified by silica gel column chromatography

Sources & evidence

ORD record: ord-84d32c72688943b284b6c7bfe39b58eb
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266879B2

Reaction notes

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