Ammonium Chloride → HCID 57901676, compound

Temperature

0 °C

To a solution of 2-(1,3-thiazol-2-yl)-1H-indole-7-carbaldehyde (0.446 g) in anhydrous tetrahydrofuran (10 mL) was added 1.0 M methylmagnesium bromide (4 mL) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. Under ice-cooling, 1.0 M methylmagnesium bromide (4 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was ice-cooled, 1.0 M methylmagnesium bromide (2 mL) was added, and the mixture was stirred at room temperature for 1 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (0.090 g, yield 19%) as colorless crystals.

1. temperaturecooling
2. temperatureUnder ice-cooling
3. stirringthe mixture was stirred at room temperature for 1 hr
4. temperaturecooled
5. stirringthe mixture was stirred at room temperature for 1 hr
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed successively with water and saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by preparative HPLC

ORD record

ord-3da177fcc758465ea356c63451160ab6

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957070B2