6 Different Diversification Groups

Product overview:

The sulfinate alkylation reaction described by Prof. Baran is a powerful late stage functionalization tool. Our kit is available in 2 sizes. A small scale kit to screen the chemistry using multiple solvents (HCK1013-01-002) and a production kit (HCK1013-01-001) to conveniently produce in one step 6 different analogues of a lead compound in mg quantities. Each reaction vial contains sulfinate alkylation reagent (pre-weighed) and a stirring bar to react with your substrate.  C-H functionalization will primarily occur on electron-deficient heteroarenes at one or several positions.

HCK1013-01-001

The typical protocol is performed at 0.142 mol/l concentration reaction condition. 2 equivalents of sulfinate reagent are preloaded (100 µmol) and 3 equivalents of TBHP is added. These reaction conditions are not air sensitive.

Recommended solvents are DMSO or CHCl₃ with or without H₂O/TFA (0.1 ml of TFA in 2 ml of water).  H₂O/TFA can change the regioselectivity and conversion of the reaction.

Prepare a solution of substrate with 300 µmol of substrate in 2.1 ml selected solvent.

1. Add 350 µl of substrate solution to each reagent vial containing the sulfinates. Shake the vial to allow reagents to mix properly.
2. If needed add 80 µl of H₂O/TFA in each vial.
3. Add 21 µl of TBHP in each vial.
4. Stir the reaction vials in the reaction block at 50°C for 12-24 hours.
5. Remove the vial caps.
6. Prepare analytical sample for each reaction condition with 5 µl sample diluted into 200 µl in either DMSO or water/acetonitrile 50/50.

Analyze resulting analytical samples by LC/MS.

Sulfinate Alkylation Solvent Effect
Substrate: Hydroquinine