Hydrochloric Acid → 2-Methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenylboronic acid
Reaction equation
C([Mg]Cl)(C)C.I[C:7]1[CH:8]=[C:9]([C:14]2[O:15][C:16]([CH3:19])=[N:17][N:18]=2)[CH:10]=[CH:11][C:12]=1[CH3:13].[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C.Cl>O1CCCC1.O>[CH3:13][C:12]1[CH:11]=[CH:10][C:9]([C:14]2[O:15][C:16]([CH3:19])=[N:17][N:18]=2)=[CH:8][C:7]=1[B:20]([OH:25])[OH:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
Isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 10 mL, 20.0 mmol) was added dropwise over 20 minutes to a stirred solution of 2-(3-Iodo-4-methylphenyl)-5-methyl-1,3,4-oxadiazole (preparation 55c, 4.0 g, 13.3 mmol) in tetrahydrofuran (40 mL) at −10° C. The mixture was stirred for 1 hour at −10° C. then triisopropyl borate (4.71 mL, 20.0 mmol) was added dropwise over 10 minutes and the mixture was stirred for 1 hour at −10° C. Then, the mixture was warmed to room temperature and stirred overnight. Water was then added, the mixture was cooled by means of an ice-water bath and the pH was adjusted to 3-4 with 2M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was triturated with diethyl ether and the solid was filtered and dried to give the title compound (1.92 g, 66%) as a white solid.
Workup
- stirringthe mixture was stirred for 1 hour at −10° C
- temperatureThen, the mixture was warmed to room temperature
- stirringstirred overnight
- temperaturethe mixture was cooled by means of an ice-water bath
- extractionThe mixture was extracted with ethyl acetate
- washthe organic layer was washed with brine
- dry with materialdried (MgSO4)
- customevaporated
- customThe residue was triturated with diethyl ether
- filtrationthe solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-0e206c4966e34cfab2b460caa8cb5285
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772288B2
Reaction notes
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