Cesium carbonate → HCID 22477513, compound

Participants

Reaction Conditions

Reaction Steps

Into a tube containing cesium carbonate (153 mg) was added (i) a solution of 4-chloro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [50 mg, Reference Example 13(i)] in 1,2-dimethoxyethane (1 mL), (ii) tris-(dibenzylideneacetone)-dipalladium(0) (15 mg) in 1,2-dimethoxyethane (0.5 mL), (iii) 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (42 mg) in 1,2-dimethoxyethane (0.5 mL) and (iv) morpholine (30 mg). This mixture was heated under agitation at 80° C. for 15 hours and then filtered on a silica plug that was then washed with dichloromethane and methanol (1 mL each). The combined filtrate plus washings were evaporated using a centrifuge evaporator. The residue was dissolved in dimethylsulfoxyde (1 mL) and then subjected to LC-MS triggered purification (injections corresponding to 20 mg crude compound) affording 4-(morpholine-4yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine which was resuspended in methanol (2 mL) and magnesium turnings (89 mg, 15 equivalents from the mass measured after evaporation of the chromatographic solvent) were added. The suspension was then agitated for 15 hours at room temperature and then filtered on Celite. The filtrate was evaporated and the residue was solubilized in dimethylsulfoxide and subjected to LC-MS triggered purification according affording the title compound. LC-MS: METHOD C: RT=3.27 minutes, 363.3[M+H]+.

Provenance & Evidence