Hydrochloric Acid → 6-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-2-(2,2,2-trifluoro-ethoxy)-nicotinonitrile

関与物質

役割	名称	HCID	仕込み量
反応物	Hydrochloric Acid	HCID 313	—
反応物	Cesium carbonate	HCID 10796	—
反応物	1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-ol	HCID 57968699	—
反応物	6-Chloro-2-(2,2,2-trifluoro-ethoxy)-nicotinonitrile	HCID 86636457	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	6-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-2-(2,2,2-trifluoro-ethoxy)-nicotinonitrile	HCID 67439865	41%

反応条件

温度	80 °C

反応手順

To a solution of 6-chloro-2-(2,2,2-trifluoro-ethoxy)-nicotinonitrile (4, 1.26 g, 5.33 mmol) in DMF (anhydrous, 30 mL) were added 3H-benzo[c][1,2]oxaborole-1,5-diol (400 mg, 2.67 mmol) and Cs2CO3 (1.91 g, 5.87 mmol). The reaction was heated at 80° C. for 2 h by microwave. After the reaction cooled to room temperature, HCl (1 M, 20 mL) was added. The volatiles were removed in vacuo. Purification was accomplished by preparative HPLC, eluting with 5%-90% ACN/water gradient, to afford 380 mg (41% yield) of the title compound as a white solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09012431B2
出典データセット	uspto-grants-2015_04
ORD ID	ord-634ad9a126a2415db756c267e4861f56
出典メモ	uspto-grants-2015_04