Potassium Phosphate, Tribasic → [2-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

温度

70 °C

A suspension of 4-bromo-2-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (635 mg, 1.75 mmol), tert-butyl carbamate (614 mg, 5.25 mmol), Pd2(dba)3 (40 mg, 0.044 mmol), Xantphos (101 mg, 0.175 mmol) and potassium phosphate tribasic (742 mg, 3.5 mmol) in toluene (15 mL) and water (3 mL) was de-gassed and purged with argon and the reaction mixture was heated at 70° C. for 5 h. The mixture was cooled and partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane) to afford the title compound as a pale yellow solid (396 mg, 57% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.19 (s, 1H), 9.05 (s, 1H), 7.92 (d, J=3.1 Hz, 1H), 7.80 (d, J=8.2 Hz, 2H), 7.72 (d, J=7.9 Hz, 1H), 1.48 (s, 9H).

1. customwas de-gassed
2. custompurged with argon
3. temperatureThe mixture was cooled
4. custompartitioned between ethyl acetate and water
5. customThe layers were separated
6. washthe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe resultant residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane)

ORDレコード

ord-6a3d03b7b2cb4987849e6ea9de6c5d21

出典データセット

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09309240B2