Reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1[C:20]([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:30].C(N(CC)CC)C.O>ClCCl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:30][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([B:21]3[O:25][C:24]([CH3:26])([CH3:27])[C:23]([CH3:29])([CH3:28])[O:22]3)[C:15]=2[CH3:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-tert-butylbenzoyl chloride (5.24 g; 26.7 mmol) in dichloromethane (40 mL) was added portionwise to a solution of 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (4) (6.22 g; 26.7 mmol) and triethylamine (5.6 mL; 40.1 mmol) in dichloromethane (60 mL) and the mixture was stirred at room temperature for 16 hr. Water (100 mL) was added and the mixture extracted with dichloromethane (3×70 mL). The combined organic layers were washed with water (2×100 mL) and brine (1×100 mL), dried over magnesium sulfate and evaporated under reduced pressure to give 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (5) as a white solid (9.7 g).
Workup
- extractionthe mixture extracted with dichloromethane (3×70 mL)
- washThe combined organic layers were washed with water (2×100 mL) and brine (1×100 mL)
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-93da54ae0a234bc19bf84bf5c7ebbdd9
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947835B2
Linked notes
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