Chlorosuccinimide → HCID 57426197, compound

HRID 1094108Notes

Reaction equation

HRID 1094108 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

HCID 31398ChlorosuccinimideHCID 57426196HCID 57426196, compound

Product 1

HCID 57426197HCID 57426197, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 (5 mL) and CHCl3 (15 mL)
  2. extractionThe aqueous phase was extracted further with CHCl3 (15 mL)
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70f36504d3774c49afd9e89125194c3c
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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