Trimethylsilane → HCID 118566595, compound

To a solution of 6-chloro-2-(3-hydroxy-prop-1-ynyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide (0.25 g, 0.62 mmol, 1.00 eq) in methanol (5 mL, 20 V) were added trimethylsilane (0.65 mL, 6.23 mmol, 10 eq) and followed by palladium on carbon (10% w/w) (0.07 g, 0.06 mmol, 0.10 eq) at 0 OC. The reaction mixture was stirred for 0.5 h. After the completion of the reaction as evidenced by TLC, the reaction mixture was concentrated under vacuum. The reaction mixture was diluted with ethyl acetate (20 mL) and extracted with water (20 mL) and brine solution (20 mL). The organic layer was separated and dried over Na2SO4 and concentrated under vacuum. The crude product was further purified by column chromatography to afford the title compound (0.08 g, 0.18 mmol, 29.0%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.82 (t, J=5.83 Hz, 1H), 7.96-8.01 (m, 2H), 7.76 (d, J=9.01 Hz, 1H), 7.55 (d, J=8.72 Hz, 1H), 4.58 (t, J=6.22 Hz, 1H), 3.46 (t, J=6.41 Hz, 2H), 3.27 (t, J=6.22 Hz, 2H), 2.95 (t, J=7.62 Hz, 2H), 2.02-2.04 (m, 2H), 1.74-1.93 (m, 7H), 1.29-1.33 (m, 2H). m/z: 397.2 [M+H]+

1. customAfter the completion of the reaction
2. concentrationthe reaction mixture was concentrated under vacuum
3. additionThe reaction mixture was diluted with ethyl acetate (20 mL)
4. extractionextracted with water (20 mL) and brine solution (20 mL)
5. customThe organic layer was separated
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under vacuum
8. customThe crude product was further purified by column chromatography

ORD record

ord-15cdd66be02c46548456349ac2c37993

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399623B2