Tri-o-tolylphosphine → 1-(2,3-Difluoro-4-hydroxy-phenyl)-2-(2-methyl-allyl)-1H-indole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-1-(2,3-difluoro-4-hydroxyphenyl)-1H-indole-3-carbonitrile (Example 103), methallyltri-n-butyltin (2 eq), Pd2(dba)3 (0.05%) and tri(o-tolyl)phosphine (20%) was dissolved in DMF, degassed with N2 and heated at 80° C. over night. The reaction mixture was quenched by addition of sat. NH4Cl, diluted with EtOAc, and washed with brine and then dried over Na2SO4. The residue was subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, and identified by 1H NMR. ES/MS m/z: 289.11 (M+H), 287.15 (M−H); 1H NMR (chloroform-d, 500 MHz): 7.76 (m, 1H), 7.28 (m, 1H), 7.23 (m, 1H), 7.17 (m, 2H), 7.13 (m, 1H), 6.98 (m, 2H), 5.86 (m, 1H), 1.98 (d, 3H, J=1.3 Hz) and 1.89 (d, 3H, J=1.2 Hz).

Provenance & Evidence