2-Dimethylaminopyridine → methyl 3,5-dichloro-4-{[4-(propanoylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoate

A stirred solution of 2,6-dichloro-4-(methoxycarbonyl)benzoic acid (600 mg, 2.3 mmol), in dimethylacetamide (10 mL) was treated with 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (1300 mg, 3.45 mmol), 1-hydroxy-7-azabenzotriazole (469 mg, 3.45 mmol), N,N-diisopropylethylamine (1.05 mL, 5.75 mmol) and dimethylaminopyridine (140 mg, 1.15 mmol) were added and the mixture was stirred at room temperature for about 1 hour. This was followed by addition of N-(1H-pyrrolo[3,2-c]pyridin-4-yl)propanamide (450 mg, 2.3 mmol) and stirring at room temperature for about 16 hours. The reaction mixture was poured into water (150 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine (100 mL) and organic layer was separated and dried over anhydrous sodium sulphate to give crude product which was purified by silica gel (100-200 mesh size) column chromatography using ethyl-acetate and hexane as eluting system to give pure methyl 3,5-dichloro-4-{[4-(propanoylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoate. (250 mg, 25%)

1. additionwere added
2. stirringstirring at room temperature for about 16 hours
3. extractionextracted with ethyl acetate (2×50 mL)
4. washThe combined organic layer was washed with brine (100 mL) and organic layer
5. customwas separated
6. dry with materialdried over anhydrous sodium sulphate
7. customto give crude product which
8. customwas purified by silica gel (100-200 mesh size) column chromatography
9. washas eluting system

ORD record

ord-825d91cbe65847dfa56a950f713d33e8

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09364466B2