ethyl 2-(4'-(4-(tert-butoxycarbonylamino)-3-methylisoxazol-5-yl)biphenyl-4-yl)acetate synthesis

6synthesis methods

Product Name:ethyl 2-(4'-(4-(tert-butoxycarbonylamino)-3-methylisoxazol-5-yl)biphenyl-4-yl)acetate
CAS Number:1284212-82-3
Molecular formula:C25H28N2O5
Molecular Weight:436.5002

859169-20-3 Synthesis

4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco

859169-20-3
106 suppliers
$17.00/100mg

tert-butyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate

1280205-96-0
3 suppliers
inquiry

ethyl 2-(4'-(4-(tert-butoxycarbonylamino)-3-methylisoxazol-5-yl)biphenyl-4-yl)acetate

1284212-82-3
2 suppliers
inquiry

Yield:1284212-82-3 48%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;sodium carbonate in 1,4-dioxane;water;Reflux;Inert atmosphere;

Steps:

VII

A flask was charged with compound VII-2 (50 mg, 0.14 mmol), compound VII-3 (82.4 mg, 0.28 mmol), Na₂C0₃ (30 mg, 0.28 mmol), dioxane/H₂0 (12 mL, v/v=5/l) and Pd(dppf)Cl₂ (20 mg, 0.03 mmol). The flask was purged with nitrogen and the mixture was refluxed overnight. After being cooled to rt, the mixture was diluted with water (10 mL), extracted with EtOAc (20 mL><3). The combined organic layer was washed with brine, dried over anhydrous Na₂S0₄, and concentrated in vacuo. The residue was purified by prep-TLC (Petroleum ether:EtOAc = 3: 1) to give compound VII-4 (30 mg, yield 48%). 1H NMR (CDC1₃, 400 MHz): δ 7.88 (d, J=7.2 Hz, 2H), 7.69 (d, J=6.4 Hz, 2H), 7.59 (d, J=6.4 Hz, 2H), 7.39 (d, J=8.4 Hz, 2 H), 5.8 (brs, 1H), 4.18 (q, 2H), 3.67 (s, 2H), 2.30 (s, 3H), 1.51 (brs, 9H), 1.28 (t, J=7.2 Hz, 3H). MS (ESI) m/z (M+H)⁺ 437.

References:

WO2013/25733,2013,A1 Location in patent:Paragraph 0454

1228689-61-9 Synthesis