Borane;tetrahydrofuran → HCID 58138929, compound
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[N:13])=[CH:7][C:6]=2[Br:14].O1CCCC1.B>C1COCC1>[F:16][C:2]([F:1])([F:15])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH2:13])=[CH:7][C:6]=2[Br:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-(trifluoromethyl)-5-cyano-7-bromo-1H-indole (Intermediate 8; 200 mg, 0.692 mmol) in THF (10 mL) cooled in an ice-water bath was treated with borane tetrahydrofuran complex (1M in THF, 1.522 mL, 1.522 mmol) dropwise via a syringe and stirred under argon for 18 hrs while allowing to warm to room temp. The reaction mixture was then quenched with methanol (5 mL) and stirred at room temperature for 10 min. The reaction mixture was then evaporated to dryness to give the title compound as a white foam (230 mg), which was used in the next step without further purification;