1,2-Dichloroethane → N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
Reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12](C(O)=O)=[CH:11][CH:10]=2)[O:3]1.C(Cl)CCl.[CH3:23][NH:24][CH3:25].C1C[O:29]CC1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[CH3:23][NH:24][C:25](=[O:29])[C:17]1[CH:16]=[CH:12][CH:11]=[CH:10][C:9]=1[B:4]1[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.0 g, 4.03 mmol), EDC (0.81 g, 4.23 mmol), and DMAP (catalytic amount) in 3 mL of DMF was stirred at room temperature for 1 hr, and then 2 mL of a 2M solution of N,N-dimethylamine in THF (4 mmol) was added into the reaction mixture. The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate (100 mL) was added and the mixture was washed with saturated sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated. The solvent was removed to give the title compound which was used without further purification for the next step. Mass Spectrum (ESI) m/e=262 (M+1).
Workup
- stirringThe resulting mixture was stirred at room temperature for 16 h
- washthe mixture was washed with saturated sodium bicarbonate and brine
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-7c638b9d186d453686c94ce59c87c438
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07358250B2
Reaction notes
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