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

HRID 2370046Notes

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-c1dfb3eca82842aa84c3d0e67299de33
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710057B2

Reaction notes

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