Triethylamine → HCID 86699739, compound

To a stirred solution of 4-bromo-2-methoxy-6-methyl-benzoic acid (synthesized according to the methods described in sections a) to d) of example 10) (2.0 g, 8.16 mmol) in dichloromethane (50 ml) are added oxalyl chloride (0.84 ml, 9.79 mmol) and dimethylformamide (catalytic amount) at 0° C. The reaction mixture is stirred for 30 min at RT. Excess oxalyl chloride is distilled off under nitrogen. The residue is dissolved in dichloromethane (20 ml), cooled to 0° C. followed by the addition of triethylamine (2.8 ml, 20.4 mmol) and 4-fluorobenzylamine (1.12 ml, 9.79 mmol). The reaction mixture is stirred for 1 h at RT. After completion of the reaction (monitored by TLC) the mixture is diluted with water (50 ml) and extracted with dichloromethane (3×50 ml). The organic layer is washed with water (50 ml), brine (50 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 15% ethyl acetate/hexane) to yield 4-bromo-N-[(4-fluorophenyl)-methyl]-2-methoxy-6-methyl-benzamide (2.70 g, 7.67 mmol, 94%).

1. distillationExcess oxalyl chloride is distilled off under nitrogen
2. dissolutionThe residue is dissolved in dichloromethane (20 ml)
3. temperaturecooled to 0° C.
4. stirringThe reaction mixture is stirred for 1 h at RT
5. customAfter completion of the reaction (monitored by TLC) the mixture
6. extractionextracted with dichloromethane (3×50 ml)
7. washThe organic layer is washed with water (50 ml), brine (50 ml)
8. dry with materialdried over anhydrous sodium sulfate
9. customevaporated
10. customto get the crude product, which
11. customis purified by column chromatography (silica gel, 15% ethyl acetate/hexane)

ORD record

ord-130267ca3a7a4ce396001c3c22985153

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2