Chlorosuccinimide → HCID 58565370, compound

HRID 2175330Notes

Reaction equation

HRID 2175330 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[C:12]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[C:17]2[CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])[CH:13]=[CH:14][CH:15]=1>CN(C=O)C.O>[Cl:1][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)[C:17]=1[CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 58565341HCID 58565341, compound

Product 1

HCID 58565370HCID 58565370, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-chlorosuccinimide (0.015 g, 0.11 mmol) in DMF (0.1 mL) was added dropwise to an ice-cooled solution of tert-butyl {1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethyl}carbamate (35 mg, 0.099 mmol) in N,N-dimethylformamide (0.5 mL, 6 mmol). The resulting mixture was allowed to warm to room temperature and stirred for an additional 4 hours. The mixture was then diluted with water and then extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-10% EtOAc in hexane) to give the desired product (36 mg, 94%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-a578d576ff4148198236eb5d9ecf79ed
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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