Chlorosuccinimide → HCID 57426197, compound
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][C:20]#[N:21])=[CH:5][N:6]2[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[Cl:22]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[C:10]([Cl:22])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][C:20]#[N:21])=[CH:5][N:6]2[CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl [4-amino-3-(cyanomethyl)-1H-indol-1-yl]acetate from Step A (150 mg, 0.526 mmol) in CH2Cl2 (5 mL) was added N-chlorosuccinimide (70 mg, 0.526 mmol). The reaction mixture was stirred at ambient temperature for 30 min, then partitioned between saturated aqueous NaHCO3 (5 mL) and CHCl3 (15 mL). The aqueous phase was extracted further with CHCl3 (15 mL) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound, which was of sufficient purity for use in the next step. MS: m/z=320 (M+1).