Acetic Acid → 2-((3-(7-Bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-methoxybenzoic acid

A mixture of 4-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide (0.184 g, 0.466 mmol), 2-formyl-5-methoxybenzoic acid (0.210 g, 1.164 mmol), sodium triacetoxyborohydride (0.296 g, 1.397 mmol), and acetic acid (0.067 mL, 1.164 mmol) in dichloromethane (14 mL) and tetrahydrofuran (14 mL) was stirred at room temperature for 16 hr. The reaction was quenched with water (30 mL) and the mixture was extracted with ethyl acetate (3×40 mL). The combined extract was washed with brine (30 ml) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the crude desired product (0.425 g, 0.760 mmol, 163% yield) as a beige solid. The crude product was used in the next step without further purification.

1. customThe reaction was quenched with water (30 mL)
2. extractionthe mixture was extracted with ethyl acetate (3×40 mL)
3. extractionThe combined extract
4. washwas washed with brine (30 ml)
5. dry with materialdried over anhydrous MgSO4
6. customRemoval of solvent under vacuum

ORD record

ord-e90dc2631de545a880baed1c836e1449

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2