Dichloromethane → HCID 72207945, compound

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[CH:6]=[CH:7][NH:8][C:9]=2[CH:10]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.C(Cl)[Cl:30]>>[ClH:30].[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[CH2:6][CH2:7][NH:8][C:9]=2[CH:10]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 13770009methyl 6-bromo-1H-indole-4-carboxylate

Product 1

HCID 72207945HCID 72207945, compound

Procedure

To a 2000 ml flask were added of methyl 6-bromo-1H-indole-4-carboxylate 54.1.A (20.0 g, 78.7 mmole), 500 ml of DCM, 100 ml of TFA and triethylsilane (19 ml, 236 mmole). The reaction was stirred at room temperature for 16 hours at which time the reaction was partitioned between 1500 ml of DCM and 500 ml of saturated sodiumbicarbonate and the solvent was removed. The crude solid was resuspended in a 1 to 1 mixture 300 ml of EtAc/hexane and then HCl added (24 ml of 4N in Dioxane, 94.4 mmole), at which time the product crashed out. The solid was collected and dried to give of methyl 6-bromoindoline-4-carboxylate HCl 54.1.B as an off white solid (19.1 g, 85% yield).