Dimethylformamide → Methyl 4-hydroxy-3-iodobenzoate

To a solution of compound 1 (200 mg, 1.077 mmol) and 2-iodopropane (322 uL, 3.23 mmol) in DMF (10 mL) was added DIEA (750 uL, 4.31 mmol). The reaction mixture was heated to 80° C. and stirred overnight. When complete by LC/MS, the reaction was cooled to room temperature, quenched with HCl (0.5 N, 30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over sodium sulfate, concentrated and dried under high vacuum. The resulting residue was purified by reverse phase chromatography using a mixture of acetonitrile and water to give compound 2 (50 mg, 20%).

1. temperatureWhen complete by LC/MS, the reaction was cooled to room temperature
2. customquenched with HCl (0.5 N, 30 mL)
3. extractionextracted with ethyl acetate (50 mL×3)
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. concentrationconcentrated
6. customdried under high vacuum
7. customThe resulting residue was purified by reverse phase chromatography
8. additiona mixture of acetonitrile and water

ORDレコード

ord-80f0f737e67947b4b5b81a32a62dcec3

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08163919B2