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

HRID 1445815Notes

Reaction equation

HRID 1445815 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:21])=[C:11]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]([CH3:21])=[C:11]([CH2:13][CH2:14][N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[N:12]=3)=[CH:4][CH:3]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 116602921-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-piperidine

Product 1

HCID 589513851-{2-[2-(4'-Methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl}-piperidineYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-piperidine (See Example 34) (0.290 g, 0.830 mmol), Pd(Ph3)4 (0.043 g, 0.037 mmol), 4-methanesulfonylphenylboronic acid (0.249 g, 1.25 mmol), 2N Na2CO3 (2.1 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}-piperidine (0.323 g, 92%).

Workup

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

Sources & evidence

ORD record
ord-2ca4e04e9a754e30a481f415e08af54b
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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