1-Methyl-4-piperidinemethanol → 7-Methyl-6-((1-methylpiperidin-4-yl)methoxy)-3-(3(trifluoromethoxy)phenyl) imidazo[1,2-b]pyridazine

HRID 2353195Notes

Reaction equation

Cl[C:2]1[C:3]([CH3:22])=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[CH3:23][N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:22][C:3]1[C:2]([O:31][CH2:30][CH:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[N:7][N:6]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=3)=[CH:9][N:10]=[C:5]2[CH:4]=1

Participants

Conditions

Temperature: 165 °C

Procedure

To the toluene (5 mL) solvent was added Compound 11 (80 mg, 0.224 mmol), (1-methylpiperidine-4-yl)methanol 14 (47.3 mg, 0.366 mmol), ligand (14.41 mg, 0.037 mmol), NaOtBu (33.3 mg, 0.347 mmol) and Pd2(dba)3 (16.77, 0.018 mmol). The resulting reaction mixture was degassed for 10 min under argon and then was heated with microwave at 165° C. Concentration and preparative TLC (10% MeOH/DCM) afforded 111.5 mg (11.2%) of Compound 7-34.

Workup

customThe resulting reaction mixture
customwas degassed for 10 min under argon
concentrationConcentration and preparative TLC (10% MeOH/DCM)

Sources & evidence

ORD record: ord-f70f3890a2d54224a9a6d1a8d2318563
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750007B2

Reaction notes

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