1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-(1-tert-butyl-3-(4-chlorobenzyl)-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)benzenesulfonamide

温度

150 °C

To a mixture of 4-iodo-N-thiazol-2-yl-benzenesulfonamide (100 mg, 0.3 mmol, 1.0 equiv), tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol, 0.04 equiv), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (19 mg, 0.033 mmol, 0.12 equiv) and 2-tert-butyl-5-(4-chloro-benzyl)-2H-pyrazole-3-ylamine (86 mg, 0.33 mmol, 1.2 equiv) in 3.7 mL of anhydrous 1,4-dioxane was added sodium tert-butoxide (79 mg, 0.82 mmol, 3.0 equiv). The vial was capped, and the reaction mixture was heated 30 min at 150° C. in the microwave. The crude reaction mixture was filtered through celite then concentrated in vacuo. The residue was taken up in chloroform-methanol, concentrated onto celite, and purified via automated flash chromatography (12 g SiO2, gradient from hexanes to ethyl acetate). The appropriate fractions were collected, concentrated in vacuo, then lyophilized from water-acetonitrile to afford the product as an off-white solid (60 mg, 40%).

1. customThe vial was capped
2. customThe crude reaction mixture
3. filtrationwas filtered through celite
4. concentrationthen concentrated in vacuo
5. concentrationconcentrated onto celite
6. custompurified
7. customThe appropriate fractions were collected
8. concentrationconcentrated in vacuo

ORDレコード

ord-d266c923de834f0784478cd24e82b61d

出典データセット

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08124610B2