ChemicalBook CAS DataBase List [3-(3,5-diMethyl-4-isoxazolyl)-4-(Methyloxy)phenyl]aMine

[3-(3,5-diMethyl-4-isoxazolyl)-4-(Methyloxy)phenyl]aMine synthesis

6synthesis methods

Product Name:[3-(3,5-diMethyl-4-isoxazolyl)-4-(Methyloxy)phenyl]aMine
CAS Number:1300031-61-1
Molecular formula:C12H14N2O2
Molecular Weight:218.25

3,5-Dimethylisoxazole-4-boronic acid pinacol ester

832114-00-8
229 suppliers
$6.00/250mg

74587-12-5 Synthesis

74587-12-5
126 suppliers
$9.00/1g

[3-(3,5-diMethyl-4-isoxazolyl)-4-(Methyloxy)phenyl]aMine

1300031-61-1
1 suppliers
inquiry

Yield: 93%

Reaction Conditions:

with palladium diacetate;caesium carbonate;triphenylphosphine in 1,2-dimethoxyethane at 90; for 16 h;Inert atmosphere;

Steps:

1.5 Intermediate step 5 toward Example 1: 3-(3,5-dimethylisoxazol-4-yl)-4-methoxy-aniline
Intermediate step 5 toward Example 1: 3-(3,5-dimethylisoxazol-4-yl)-4-methoxy-aniline [00231] Pd(OAc)₂ (1.42 g, 6.34 mmol) and PPh₃ (3.33 g, 12.7 mmol) were weighed into a 2-necked flask equipped with a reflux condenser, and the flask was flushed with N₂ gas. Degassed DME (60.0 mL) was added, and the mixture was stirred for 30 m at rt. 3,5-Dimethyl- 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoxazole (34.0 g, 152 mmol), 3-iodo-4- methoxy-aniline (15.8 g, 63.4 mmol), and Cs₂C0₃ (51.7 g, 159 mmol) were weighed into a second flask, and the flask was flushed with N₂ gas. Degassed DME (300 mL) and degassed water (30.0 mL) were added. The mixture was stirred for 20 m and then added to the first flask. The second flask was rinsed with degassed DME (15.0 mL), and the liquid was transferred to the first flask. The resulting mixture was heated to 90°C for 16 h and then cooled to rt. The mixture was diluted with saturated aq NaHC0₃ (100 mL) and EtOAc (100 mL), and the aq phase was extracted with EtOAc (3X150 mL). The combined organic phases were dried over MgS0₄, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography on silica gel, eluting with mixtures of EtOAc and hexanes to provide the title compound as a solid (12.9 g, 93%). 1H NMR (500 MHz, CDC1₃) δ 6.80 (d, J = 8.7 Hz, 1H), 6.69 (dd, J = 8.6, 2.9 Hz, 1H), 6.48 (d, J = 2.9 Hz, 1H), 3.70 (s, 3H), 3.49 (s, 2H), 2.29 (s, 3H), 2.16 (s, 3H); [M+H]+ 219.3.

References:

EPIGENETIX, INC.;ALBERT, Jeffrey, S.;JOHNSTONE, Shawn;JONES, Paul WO2014/152029, 2014, A2 Location in patent:Paragraph 00231