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| Description | 4-Chloro-2-methoxyphenylboronic acid is a biochemical reagent that can be used as a biomaterial or organic compound for life science related research. |
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Uses |
suzuki reaction. 4-Chloro-2-methoxyphenylboronic acid is a boronic acid derivative with specific substituents on the phenyl ring. Boronic acids are known for their utility in organic synthesis, particularly in reactions like Suzuki-Miyaura cross-coupling reactions. |
| Canonical SMILES | B(C1=C(C=C(C=C1)Cl)OC)(O)O |
| Exact Mass | 186.0255020 g/mol |
| Monoisotopic Mass | 186.0255020 g/mol |
| Complexity | 145 |
1-(3-{[4-(4-Chloro-2-methoxyphenyl)-1,3,5-triazin-2-yl]amino}phenyl)methanesulfonamide (15): A mixture of crude 3-[(4-chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide (174 mg), 4-chloro-2-methoxyphenylboronic acid (116 mg, 0.62 mmol) and K3PO4 (217 mg, 1.02 mmol) in dioxane/water (10:1, 10 mL) was degassed with a stream of nitrogen for 15 min. Pd(dppf)Cl2⋅CH2Cl2 (28 mg, 0.03 mmol) was added and the reaction mixture was heated for 90 min at 145 °C in a microwave oven. The mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by preparative HPLC (acidic conditions) to give 15 as a light beige solid (13 mg, 0.03 mmol): 1H NMR (400 MHz, [D6]DMSO): δ=3.90 (s, 3 H), 4.24 (s, 2 H), 6.86 (br s, 2 H), 7.08 (d, 1 H), 7.15 (d, 1 H), 7.28 (d, 1 H), 7.36 (t, 1 H), 7.74 (s, 1 H), 7.88 (m, 2 H), 8.81 (s, 1 H), 10.44 ppm (s, 1 H); MS (ESI) m/z: 406 [M+H]+.
An alternative route, illustrated in Scheme 4 and featuring an additional homologation step, was employed for the preparation of M4K2308 (32) and M4K2281 (33). The ring closure approach used for the preparation of 32 and 33 had to be completely reformulated from previous synthetic strategies due to the formation of a styrene when using SNAr reaction conditions. Commercially available 9 and 4-chloro-2-methoxyphenylboronic acid (23) were coupled under Suzuki–Miyaura conditions to afford intermediate 24.
A mixture of crude 3-[(4-chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide (174 mg), 4-chloro-2-methoxyphenylboronic acid (116 mg, 0.62 mmol) and K3PO4 (217 mg, 1.02 mmol) in dioxane/water (10:1, 10 mL) was degassed with a stream of nitrogen for 15 min.
2-bromo-5-chloroanisole
Trimethyl borate
4-(4-chloro-2-methoxyphenyl)pyridine 1-oxide
2-[3-(4-chloro-2-methoxyphenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[1-methyl-1-(3-trifluoromethyl-phenyl)ethyl]-acetamide
(4-chloro-2-hydroxyphenyl)boronic acid
C25H25ClN4O2
CAS:126747-14-6
