Sodium Carbonate → HCID 68701677, compound

HRID 1445839Notes

Reaction equation

HRID 1445839 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[C:17]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)(=[O:19])[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[OH:15][CH2:14][CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([C:17](=[O:19])[CH3:18])[CH:25]=3)=[CH:3][CH:4]=2)[O:9][C:10]=1[CH3:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

Product 1

HCID 68701677HCID 68701677, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (0.200 g, 709 mmol) [which is obtained by the method of D. Brooks, J. Med. Chem., 2001, 44, 2061-2064 or see WO 0116120], Pd(Ph3)4 (0.036 g, 0.031 mmol), 3-acetylphenylboronic acid (0.174 g, 1.06 mmol), 2N Na2CO3 (1.8 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 1-{4′-[4-(2-hydroxy-ethyl)-5-methyl-oxazol-2-yl]-biphenyl-3-yl}-ethanone (0.188 g, 83%).

Workup

  1. customis obtained by the method of D
  2. customirradiation at 30 W, 90° C. for 30-45 minutes
  3. concentrationConcentrate
  4. custompurify on silica gel eluting with 10% 2N NH3 in methanol/dichloromethane

Sources & evidence

ORD record
ord-09ade4c0c27f4190bd37d3beba675c3e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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