1,4-Cyclohexadiene → HCID 67461278, compound

HRID 1777717Notes

Reaction equation

C([N:8](CC1C=CC=CC=1)[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[C:31]([F:34])([F:33])[F:32])C1C=CC=CC=1.C1CC=CCC=1>CCO.[OH-].[OH-].[Pd+2]>[N:25]1([C:17]2[N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH2:8])=[C:10]([C:31]([F:33])([F:32])[F:34])[CH:11]=3)[CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][CH:21]=[N:22]3)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of dibenzyl-[4-(5-morpholin-4-yl-[1,6]naphthyridin-7-yl)-2-trifluoromethyl-phenyl]-amine, 4 (29.1 mg, 0.06 mmol, 1 eq) in dry EtOH (3 mL) was added Pd(OH)2 (15 mg, 50% w/w) and 1,4-cyclohexanediene (110 μL, 1.15 mmol, 20 eq) under Ar(g). The mixture was heated at 80° C. overnight. More Pd(OH)2 (15 mg, 50% w/w) and 1,4-cyclohexanediene (110 mL, 1.15 mmol, 20 eq) were 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 with hexane/EtOAc (0:1) to yield the product as a pale yellow solid (10.0 mg, 51%).

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 with hexane/EtOAc (0:1)

Sources & evidence

ORD record: ord-bd7a355791664a759f061b36b945ea65
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266879B2

Reaction notes

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