Sodium Sulfite → 4,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1H-indole-3-carboxylic acid

To a solution of 4,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1H-indole-3-carbaldehyde (40 mg, 0.122 mmol) in acetonitrile (2.3 mL), t-butanol (2.3 mL) and 2-methyl-2-butene (1.5 mL) was added a solution of sodium chlorite (164 mg, 2.43 mmol) and sodium dihydrogen phosphate (335 mg, 2.43 mmol) in water (2.3 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with a solution of sodium sulfite (337 mg, 2.68 mmol) in water (5.0 mL), and extracted with ethyl acetate (10 mL×3). The organic layers were washed with brine (10 mL) and dried over sodium sulfate, filtered and concentrated to give a crude residue, which was purified by reverse phase HPLC to give the title compound (14.6 mg, 42%) as a white solid.

1. extractionextracted with ethyl acetate (10 mL×3)
2. washThe organic layers were washed with brine (10 mL)
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a crude residue, which
7. customwas purified by reverse phase HPLC

ORD record

ord-a3b3c8448e88472db6294f25fbb6db52

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2