Methyl iodide → 3-iodo-1,5,5-trimethyl-4,5,6,7-tetrahydro-1H-indazole

온도

0 °C

In a round-bottomed flask, 3-iodo-5,5-dimethyl-4,5,6,7-tetrahydro-1H-indazole (642 mg, 2.33 mmol) was dissolved in THF (8.5 ml). The solution was cooled to 0° C. and potassium tert-butoxide (365 mg, 3.26 mmol) was added. The reaction mixture was stirred at 0° C. for 40 min then methyl iodide (0.18 ml, 2.88 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 1.5 h then quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/Hexanes (gradient 0-15% EtOAc) to provide 497 mg (74%) of 3-iodo-1,5,5-trimethyl-4,5,6,7-tetrahydro-1H-indazole as a white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 3.76 (s, 3H), 2.53 (t, J=6.4 Hz, 2H), 2.11 (s, 2H), 1.58 (t, J=6.6 Hz, 2H), 0.99 (s, 6H).

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringstirred for 1.5 h
3. customthen quenched with water
4. extractionextracted with EtOAc (2×)
5. washThe combined organic layers were washed with water and brine
6. dry with materialthen dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was chromatographed over silica gel with EtOAc/Hexanes (gradient 0-15% EtOAc)

ORD 기록

ord-3f2cbe88a32f4fcfada3140a01565d1a

출처 데이터셋

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08658646B2