* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 100.0℃; for 36h;
To a mixture of the product from Step 1, -bromo-4-iodo-2-methoxybenzene (750 mg, 2.4 mmol), CsF (1.09 g, 7.2 mmol), <strong>[850568-47-7](2-amino-4-cyanophenyl)boronic acid hydrochloride</strong> (390 mg, 2.4 mmol), and Pd(PPh3)4 (277 mg, 0.24 mmol) was added DME (15 mL) under nitrogen. It was then heated to 100C. After 36 hours, EtOAc and water were added to the resulting thick red suspension. The organic layer was washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified on silica (gradient EPO <DP n="52"/>elution, 3-50% EtO Ac/hex anes) to yield the title compound as a red oil. LRMS (M+H)+ =303.1.
With cesium fluoride;Pd(PPh3)4; In 1,2-dimethoxyethane; water; ethyl acetate;
Step 2: 2-amino-4'-bromo-3'-methoxybiphenyl-4-carbonitrile To a mixture of the product from Step 1, -bromo-4-iodo-2-methoxybenzene (750 mg, 2.4 mmol), CsF (1.09 g, 7.2 mmol), <strong>[850568-47-7](2-amino-4-cyanophenyl)boronic acid hydrochloride</strong> (390 mg, 2.4 mmol), and Pd(PPh3)4 (277 mg, 0.24 mmol) was added DME (15 mL) under N2. It was then heated to 100 C. After 36 h, to the thick red suspension was added EtOAc and water. The organic layer was washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified on silica (gradient elution, 3-50% EtOAc/hex) to yield the title compound as a red oil. LRMS (M+H)+=303.1.
With potassium carbonate; triphenylphosphine;PdCl2(PPh3)2; PdCl2[dppf]; In 1,4-dioxane; ethyl acetate;
Step 2: ethyl 2-(4-bromo-3-methoxyphenyl)cyclohex-1-ene-1-carboxylate To a solution of the product from Step 1, ethyl 2-[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-ene-1-carboxylate (6.65 g, 22.0 mmol) in dioxane (125 mL) was added potassium carbonate (4.56 g, 33.0 mmol), PPh3 (0.346 g, 1.32 mmol), bis(pinacolato)diboron (6.15 g, 24.20 mmol), and PdCl2(PPh3)2 (0.463 g, 0.66 mmol). The mixture was then heated to 80 C. overnight. This solution was then cooled to r.t. and added to a mixture of 1-bromo-4-iodo-2-methoxybenzene (6.86 g, 21.92 mmol), PdCl2(dppf) (0.481 g, 0.657 mmol), potassium carbonate (9.09 g, 65.7 mmol). This mixture was then heated to 80 C. overnight. The mixture was then cooled to r.t., diluted with EtOAc (300 mL) and washed with brine and aqueous KHSO4. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo. The crude material was then purified on silica (100% DCM) to give impure product which was repurified on silica (gradient elution, 5-20% EtOAc/hexanes) to give the title compound.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
