(2,3-Dihydro-1-benzofuran-5-yl)boronic acid → (R)-tert-butyl 3-(3-(2,3-dihydrobenzofuran-5-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate (650 mg, 1 mmol) was added to a vial containing 2,3-dihydrobenzofuran-5-ylboronic acid (180 mg, 1.1 mmol) and tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol). After purging the vial with nitrogen gas, dioxane (3 mL) and 2M sodium carbonate (1.5 mL) was added to the vial respectively. The reaction mixture was stirred and was heated to 80° C. for overnight. Upon completion, the mixture was concentrated under vacuo. Water (10 mL) was added and was extracted using dichloromethane (3×25 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was purified using flash chromatography.

1. customAfter purging the vial with nitrogen gas, dioxane (3 mL) and 2M sodium carbonate (1.5 mL)
2. additionwas added to the vial respectively
3. concentrationUpon completion, the mixture was concentrated under vacuo
4. additionWater (10 mL) was added
5. extractionwas extracted
6. customdried
7. filtrationThe resulting suspension was filtered
8. concentrationconcentrated
9. customThe crude product was purified

ORDレコード

ord-3d32aefa722d46a3a02248cbf0461f8c

出典データセット

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08999957B2