Potassium Carbonate → 3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-5-methyl-phenol

온도

140 °C

5-tert-Butyl-2H-pyrazol-3-ylamine (1.11 g, 8.00 mmol), potassium carbonate (2.32 g, 16.8 mmol), copper (I) iodide (0.076 g, 0.40 mmol), and 3-bromo-5-methylphenol (1.80 g, 9.60 mmol) were weighed into a large microwave vial. This was then purged with argon then trans-N,N-dimethylcyclohexane-1,2-diamine (0.25 mL, 1.60 mmol) added. To this mixture was then added degassed toluene (8 mL). The mixture was then purged with argon again, the vial sealed, and heated for 1 h at 140° C. in the microwave, then a further 4 h at 135° C. The mixture was cooled, diluted with ethyl acetate and passed through a pad of celite/silica, washing with more ethyl acetate. The dark solution was concentrated in vacuo. The residue was purified by FCC, using 0-40% DCM in EtOAc, to give the title compound (966 mg, 49%). 1H NMR (300 MHz, CDCl3): 1.32 (9H, s), 2.24 (3H, s), 3.82 (2H, br s), 5.49 (1H, s), 6.45-6.52 (1H, m), 6.65-6.71 (1H, m), 6.85-6.91 (1H, m).

1. customThis was then purged with argon
2. additionTo this mixture was then added
3. customdegassed toluene (8 mL)
4. customThe mixture was then purged with argon again
5. customa further 4 h
6. customat 135° C
7. temperatureThe mixture was cooled
8. additiondiluted with ethyl acetate
9. washwashing with more ethyl acetate
10. concentrationThe dark solution was concentrated in vacuo
11. customThe residue was purified by FCC

ORD 기록

ord-4215267d3a574be5b64334d33dcb7b6a

출처 데이터셋

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09181242B2