Sodium hydride → (2E)-3-[4-(tert-Butyl)phenyl]-N-[1-(2-methoxyethyl)indol-6-yl]prop-2-enamide

HRID 730273Notes

Reaction equation

HRID 730273 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][NH:22]3)=[CH:18][CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27][O:28][CH2:29][CH2:30]Br>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][N:22]3[CH2:30][CH2:29][O:28][CH3:27])=[CH:18][CH:17]=2)=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 44435882HCID 44435882, compound

Product 1

HCID 10287166(2E)-3-[4-(tert-Butyl)phenyl]-N-[1-(2-methoxyethyl)indol-6-yl]prop-2-enamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round-bottomed flask was added, (2E)-3-[4-(tert-butyl)phenyl]-N-indol-6-ylprop-2-enamide, Example 189, (320 mg, 1.0 mmol) and anhydrous DMF (20 mL). The solution was stirred magnetically and treated with sodium hydride (0.10 g, 2.5 mmol, 60% dispersion in mineral oil, Aldrich) followed by 2-bromoethyl methyl ether (140 mg, 1.0 mmol, Aldrich). Stirring was continued at 25° C. for 2 h, then the reaction mixture was quenched by the addition of water (50 mL) and extracted with EtOAc. The organic extract was concentrated in vacuo. Purification by silica gel chromatography (60:40 hexane:EtOAc) provided the title compound as a yellow solid. MP 133° C. MS (ESI, pos. ion) m/z: 377 (M+1).

Workup

  1. additionTo a round-bottomed flask was added
  2. stirringStirring
  3. customthe reaction mixture was quenched by the addition of water (50 mL)
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. concentrationwas concentrated in vacuo
  7. customPurification by silica gel chromatography (60:40 hexane:EtOAc)

Sources & evidence

ORD record
ord-29870b5c32364df9bcebf118ae11f8e6
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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