Pinacol → 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine
Reaction equation
C([NH:4][C:5]1[C:6]([N+:14]([O-])=O)=[C:7]([B:11]([OH:13])[OH:12])[CH:8]=[CH:9][CH:10]=1)(=O)C.O[C:18]([C:21](O)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>Cl.O1CCOCC1.C(O)(=O)C.[Pd]>[NH2:14][C:6]1[C:7]([B:11]2[O:12][C:21]([CH3:23])([CH3:22])[C:18]([CH3:20])([CH3:19])[O:13]2)=[CH:8][CH:9]=[CH:10][C:5]=1[NH2:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
A solution of (3-acetamido-2-nitrophenyl)boronic acid (300 mg) in 2M aqueous hydrochloric acid solution (4 mL) was heated at 80° C. for 20 min. After cooling to room temperature, the solvent was reduced in vacuo to give a brown solid which was redissolved in 1,4-dioxane (5 mL). Pinacol (316 mg) was added and the mixture heated at 100° C. for 30 min. After cooling to room temperature the solvent was reduced in vacuo to give a beige solid which was dissolved in acetic acid (5 mL). Palladium on carbon (100 mg) was added and the mixture stirred under an atmosphere of hydrogen at 40° C. for 1 h. The reaction mixture was then filtered through Celite and the filtrate reduced in vacuo. Purification by column chromatography gave 2-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.
Workup
- customto give a brown solid which
- temperaturethe mixture heated at 100° C. for 30 min
- temperatureAfter cooling to room temperature the solvent
- customto give a beige solid which
- filtrationThe reaction mixture was then filtered through Celite
- customPurification by column chromatography
Sources & evidence
- ORD record
- ord-a481838d3d8647999116ff70850675df
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802670B2
Reaction notes
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