Sodium Carbonate → 1-{2-[2-(4'-Methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine

HRID 1445817Notes

Reaction equation

HRID 1445817 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]3[CH3:21])[N:12]=2)=[CH:4][CH:3]=1.[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH3:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]([CH3:22])=[C:11]([CH2:13][CH2:14][N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]4[CH3:21])[N:12]=3)=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 115160701-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine

Product 1

HCID 589514871-{2-[2-(4'-Methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidineYield 34.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine (0.290 g, 0.798 mmol), Pd(Ph3)4 (0.041 g, 0.035 mmol), 4-methanesulfonylphenylboronic acid (0.240 g, 1.20 mmol), 2N Na2CO3 (1.98 mL), and 1,4-dioxane (1 mL) to a microwave vessel. Microwave at 30 W, 90° C. for 30-45 minutes. Concentrate and purify on silica gel eluting with 10% 2N NH3 in methanol/dichloromethane to give 1-{2-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine (0.120 g, 34%).

Workup

  1. concentrationConcentrate
  2. custompurify on silica gel eluting with 10% 2N NH3 in methanol/dichloromethane

Sources & evidence

ORD record
ord-50173a46da7d451284f8da6581ae0098
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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