Chloroacetyl chloride → 2-Chloro-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide

HRID 268762Notes

Reaction equation

HRID 268762 reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][N:12]3[Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:27][CH2:28][C:29]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[Si:17]([CH:21]([CH3:23])[CH3:22])([CH:24]([CH3:26])[CH3:25])[CH:18]([CH3:19])[CH3:20])=[O:30]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 59831613Phenyl-(1-triisopropylsilanyl-1H-indol-4-yl)-amine

Product 1

HCID 598318082-Chloro-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamideYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of phenyl-(1-triisopropylsilanyl-1H-indol-4-yl)-amine XXI (1.09 g, 3 mmol) and TEA (1.35 ml, 9.7 mmol) in DCM (20 ml) was added 2-chloroacetyl chloride (773 μl, 9.7 mmol). The mixture was stirred for 5 minutes and then refluxed for 3 hours. The reaction was cooled to room temperature and partitioned between H2O and DCM. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 2-chloro-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide XXII as an off-white solid (775 mg, 59% yield).

Workup

  1. temperaturerefluxed for 3 hours
  2. custompartitioned between H2O and DCM
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-192da5d30aae484392ec8c0c3f172754
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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