Sodium Carbonate → 4-(4-{5-Methyl-4-[2-(2-methyl-piperidin-1-yl)-ethyl]-oxazol-2-yl}-phenyl)-pyridine

HRID 1445837Notes

Reaction equation

HRID 1445837 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.[N:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH3:22][C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:26]3[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=3)=[CH:3][CH:4]=2)=[N:12][C:11]=1[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[CH3:21]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 115160701-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine

Product 1

HCID 589514794-(4-{5-Methyl-4-[2-(2-methyl-piperidin-1-yl)-ethyl]-oxazol-2-yl}-phenyl)-pyridineYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl }-2-methylpiperidine (0.724 g, 1.99 mmol), Pd(Ph3)4 (0.101 g, 0.088 mmol), 4-pyridylboronic acid (0.367 g, 2.99 mmol), 2N Na2CO3 (5 mL), and 1,4-dioxane (1.5 mL) to a microwave vessel. Subject the reaction mixture to microwave irradiation 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 4-(4-{5-methyl-4-[2-(2-methyl-piperidin-1 -yl)-ethyl]-oxazol-2-yl}-phenyl)-pyridine (0.059 g, 10%).

Workup

  1. customirradiation at 30 W, 90° C. for 30-45 minutes
  2. concentrationConcentrate
  3. custompurify on silica gel eluting with 10% 2N NH3 in methanol/dichloromethane

Sources & evidence

ORD record
ord-ef5326a928564ed2889e6dd9eb6b11e6
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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