2-Bromobenzyl alcohol → HCID 68689944, compound

Temperature

-78 °C

To a −78° C. solution of (2-bromo-phenyl)-methanol (2.27 g, 12.14 mmol) in tetrahydrofuran (100 ml) was added tert-butyllithium (1.7 M in hexanes, 15.7 ml, 26.69 mmol). The reaction mixture was stirred for 10 minutes at −78° C. A solution of 2,2-dimethyl-propionic acid 5-bromo-3-formyl-pyrrolo[2,3-b]pyridin-1-ylmethyl ester (2.06 g, 6.07 mmol) in tetrahydrofuran (30 ml) was added to the stirring reaction mixture. After the reaction mixture was allowed stirred for an additional 20 minutes at −78° C., the reaction was quenched with saturated, aqueous sodium bicarbonate solution. The quenched solution was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the mixture was concentrated in vacuo. The crude material was purified by flash chromatography (0-100% ethyl acetate in hexanes) to give 1.60 g (59%) of 2,2-dimethyl-propionic acid 5-bromo-3-[hydroxy-(2-hydroxymethyl-phenyl)-methyl]-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 446.0, 448.0 (M+H+).

1. stirringAfter the reaction mixture was allowed stirred for an additional 20 minutes at −78° C.
2. customthe reaction was quenched with saturated, aqueous sodium bicarbonate solution
3. extractionThe quenched solution was extracted with ethyl acetate
4. dry with materialThe organic layer was dried over magnesium sulfate
5. concentrationthe mixture was concentrated in vacuo
6. customThe crude material was purified by flash chromatography (0-100% ethyl acetate in hexanes)

ORD record

ord-58ecb76eb2ad44c6938acf6c685a3895

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709645B2