2,6-Dichlorobenzoyl chloride → N-(3-fluoropyridin-4-yl)-2,6-dichlorobenzamide

To a cooled (0° C.) mixture of 3-fluoropyridin-4-amine (1.0 g, 8.9 mmol) and DIPEA (2.7 mL, 18 mmol) in dichloromethane (20 mL) and MeCN (10 mL) was added a solution of 2,6-dichlorobenzoyl chloride (2.1 g, 9.8 mmol) in dichloromethane (20 mL). The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was partitioned between EtOAc (30 mL) and sat. NaHCO3 (30 mL). The aqueous layer was extracted with EtOAc (2×15 mL) and then the combined organic extracts were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc) to afford N-(3-fluoropyridin-4-yl)-2,6-dichlorobenzamide (1.2 g, yield: 47%). 1H NMR (400 MHz, DMSO) δ 11.21 (s, 1H), 8.59 (d, J=2.8, 1H), 8.41 (d, J=5.4, 1H), 8.21 (dd, J=6.7, 5.4, 1H), 7.77-7.33 (m, 3H). LCMS (ESI) m/z: 285.2 [M+H+]

1. temperatureTo a cooled
2. concentrationconcentrated under reduced pressure
3. customThe residue was partitioned between EtOAc (30 mL) and sat. NaHCO3 (30 mL)
4. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
5. concentrationthe combined organic extracts were concentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (EtOAc)

ORDレコード

ord-ac4191c165004976b2b536ab8378f3fd

出典データセット

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08486950B2