DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE synthesis
- Product Name:DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE
- CAS Number:909391-56-6
- Molecular formula:C15H24BNO2
- Molecular Weight:261.17
124-40-3
214360-74-4
909391-56-6
Step X1 Intermediate XI.1: 2-(3-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (297 mg, 1.0 mmol) was dissolved in acetonitrile (5 mL), a methanol solution of dimethylamine (2 M, 1.0 mL, 2.0 mmol) was added followed by potassium carbonate (691 mg, 5.0 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, acetonitrile was removed under vacuum and the residue was partitioned with ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered and the filtrate was concentrated to afford dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine (Intermediate XI.1) as a viscous oily substance (200 mg, 0.77 mmol, 77% yield). Characterization data for intermediate XI.1: 1H NMR (300 MHz, CD3OD): δ 7.70 (m, 2H), 7.30-7.45 (m, 2H), 3.50 (s, 2H), 2.28 (s, 6H), 1.36 (s, 12H) ppm; MS (ESI), m/z: 262 ([M + H]+).
124-40-3
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214360-74-4
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909391-56-6
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$27.00/250mg
Yield: 77%
Reaction Conditions:
with potassium carbonate in acetonitrile at 20; for 16 h;
Steps:
XI
Procedure Xl INTERMEDIATE XI.1 : Dimethyl-r3-(4,4,5,5-tetramethyl-ri ,3,21-dioxaborolan-2- vDbenzyllamineTo a solution of 3-bromomethylphenyl boronic acid pinacol ester (Combi Block Inc., 297 mg, 1.0 mmol) in acetonitrile (5 ml.) was added dimethylamine (2M solution in methanol, EPO
References:
AKZO NOBEL N.V.;PHARMACOPEIA DRUG DISCOVERY, INC. WO2006/95014, 2006, A1 Location in patent:Page/Page column 43-44
103-83-3
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25015-63-8
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878197-87-6
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$45.00/100mg
909391-56-6
63 suppliers
$27.00/250mg