Ethyl Acetate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-(2-hydroxy-ethyl)-3,5-bis-trifluoromethyl-benzamide

The solution of methyl 2-(N-(4-(2-chlorophenyl)pyridin-3-yl)-3,5-bis(trifluoromethyl)benzamido)acetate (0.15 g, 0.29 mmol, example 88) in methanol (2.00 mL) was cooled down to 0° C. To the light yellow suspension was added NaBH4 (22.0 mg, 0.58 mmol) and the reaction was stirred for 2 h at room temperature. The reaction mixture was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). The product containing fractions were combined and partially evaporated upon which crystallisation started. The supernatant light brown solution was pipetted off and the remaining solid dried under high vacuum. Colorless crystals (0.024 g; 16%). MS (ESI): m/z=489.08 [M+H]+.

1. customthe layers were separated
2. extractionThe aqueous layer was extracted twice with EtOAc
3. washThe organic layers were washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. additiontreated with silica gel
7. customevaporated
8. customThe compound was purified by silica gel chromatography on a 10 g column
9. washeluting with a gradient of n-heptane:EtOAc (100:0 to 30:70)
10. additionThe product containing fractions
11. custompartially evaporated upon which crystallisation
12. customthe remaining solid dried under high vacuum

ORD record

ord-a7b7acdfe753408a91fdf277aba06235

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987307B2