Toluene → 5-Methyl-1-tosyl-7-vinyl-1H-indole-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7-chloro-5-methyl-1-tosyl-1H-indole-4-carbaldehyde (Example 110-E) (73 mg, 0.210 mmol) and vinylboronic anhydride pyridine complex (152 mg, 0.630 mmol) and K2CO3 (290 mg, 2.09 mmol) in toluene (1.7 mL) water (0.7 mL) Pd(OAc)2 (4.71 mg, 0.021 mmol) and S-Phos (CAS#657408-07-6) (17.2 mg, 0.042 mmol) were added, and the reaction was stirred at 80° C. After 1 hour the reaction was diluted with EtOAc. The organics were washed with water, dried over MgSO4, filtered and concentrated. The mixture was loaded onto silica gel and purified by flash chromatography (0-40% EtOAc in heptanes) to the title compound. MS (ESI+) m/z 340.1 (M+H).

Provenance & Evidence