Iodoethane → HCID 70562623, compound

HRID 1477884Notes

Reaction equation

HRID 1477884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([C:11]2[CH:15]=[N:14][NH:13][N:12]=2)[CH2:9][CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:40][CH3:41]>CN(C=O)C.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([C:11]2[CH:15]=[N:14][N:13]([CH2:40][CH3:41])[N:12]=2)[CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 70564996HCID 70564996, compound

Product 1

HCID 70562623HCID 70562623, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of tert-butyl 1-(1-(4-chlorophenyl)-1-(2H-1,2,3-triazol-4-yl)propyl)-1H-indol-4-ylcarbamate (150 mg, 0.33 mmol) in DMF (5 mL), was added potassium carbonate (91 mg, 0.66 mmol) and iodoethane (62 mg, 0.40 mmol). After stirring for 2 hours, the mixture was diluted with saturated aqueous ammonium chloride (10 mL) and extracted with EA. The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered, and the solvent was removed in vacuo to afford the crude product. The product was purified via column chromatography (50% EtOAc/hexanes) to provide the title product.

Workup

  1. extractionextracted with EA
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customto afford the crude product
  7. customThe product was purified via column chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c89a28b4f6d743348271321038645298
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

Loading…