Sodium Carbonate → 5'-(3,5-Dimethylisoxazol-4-yl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dimethylisoxazol-4-ylboronic acid (159 g, 1.13 mol), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) (23.6 g, 29 mmol), 5′-bromospiro[[1,3]dioxolane-2,3′-indolin]-2′-one (236 g, 0.87 mol) and Na2CO3 (184 g, 1.7 mol) in dioxane/H2O (1200 mL/300 mL) was heated to 110° C. for 12 h. The mixture was filtered through a pad of celite and concentrated in vacuo. The crude product was dissolved in CH2Cl2 (2 L), then hexane 2 L was added and the mixture was filtered again, the organic phase was concentrated in vacuo to give target product (150 g, 60%). 1H NMR (400 MHz, DMSO-d6): δH 10.56 (s, 1H), 7.31-7.33 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 4.27-4.35 (m, 4H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 287.

Provenance & Evidence