Benzyl mercaptan → 5-(Benzylsulfanyl)-6-methyl-1H-indazole

5-Bromo-6-methyl-1H-indazole (4-1, 2 g, 9.48 mmol), XANTPHOS (0.548 g, 0.948 mmol), and Pd2(dba)3 (0.868 g, 0.948 mmol) were added to an oven-dried sealed tube followed by anhydrous Dioxane (31.6 ml), DIPEA (3.31 ml, 18.95 mmol) and BENZYL MERCAPTAN (1.177 ml, 9.95 mmol). Placed in 120° C. bath. After 2 h, UPLC showed >52% P1 at 1.25 min, 15% R1 at 1.07 min, 16% byproduct at 1.56 min and several minor peaks each less than 7%. After an additional 2 h, UPLC showed no change. Cooled to RT, filtered through Celite, washed with EtOAc, concentrated to give a clear, orange oil. Dissolved in 5 mL DCM, purified by normal-phase ISCO (80 g column, 0-50% EtOAc:Hex) to give 4-3 as a yellow solid.

1. customsealed tube
2. customPlaced in 120° C.
3. customat 1.25 min
4. waitAfter an additional 2 h
5. filtrationfiltered through Celite
6. washwashed with EtOAc
7. concentrationconcentrated
8. customto give a clear, orange oil
9. custompurified by normal-phase ISCO (80 g column, 0-50% EtOAc:Hex)

ORD-Eintrag

ord-ca1f364953f6488abc3223504519c811

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09388179B2