6-bromo-3-iodo-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole → 6-Bromo-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

A solution of 6-bromo-3-iodo-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (3.0 g, 5.95 mmol) in tetrahydrofuran (40 mL) was cooled at −78° C. To this was added isopropylmagnesium chloride (2.0N solution in tetrahydrofuran, 3.12 mL, 6.2 mmol) dropwise over five minutes. The reaction mixture was stirred at this temperature for 1.5 hours and then quenched with saturated aqueous ammonium chloride solution (1 mL). The reaction mixture was then diluted with 25 mL water and extracted with ethyl acetate (150 mL). The organic layer was separated, washed with water (50 mL) then brine (50 mL), dried over sodium sulfate, filtered, and the concentrated in vacuo to afford a yellow oil, which was used in the next step without any further purification (2.2 g, 100%).

1. customquenched with saturated aqueous ammonium chloride solution (1 mL)
2. additionThe reaction mixture was then diluted with 25 mL water
3. extractionextracted with ethyl acetate (150 mL)
4. customThe organic layer was separated
5. washwashed with water (50 mL)
6. dry with materialbrine (50 mL), dried over sodium sulfate
7. filtrationfiltered
8. concentrationthe concentrated in vacuo
9. customto afford a yellow oil, which
10. customwas used in the next step without any further purification (2.2 g, 100%)

ORD record

ord-71ae06c277e24093b6ba0cefa6ee431c

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440976B2