Methyl iodide → 4-Tert-butyl-2-{5-[(3-cyano-5-methoxyindol-1-yl)methyl]benzofuran-2-yl}thiazole

HRID 1604670Notes

Reaction equation

HRID 1604670 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=5)[C:22]([C:30]#[N:31])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CI.[C:34](=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:34])=[CH:26][CH:27]=5)[C:22]([C:30]#[N:31])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 196037114-Tert-butyl-2-{5-[(3-cyano-5-hydroxyindol-1-yl)methyl]benzofuran-2-yl}thiazole

Product 1

HCID 196037754-Tert-butyl-2-{5-[(3-cyano-5-methoxyindol-1-yl)methyl]benzofuran-2-yl}thiazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-tert-butyl-2-{5-[(3-cyano-5-hydroxyindol-1-yl)methyl]benzofuran-2-yl}thiazole (158 mg), methyl iodide (0.1 ml) and sodium carbonate (0.1 g) in N,N-dimethylformamide (1.5 ml) was stirred for 3 days at room temperature. The resulting mixture was diluted with brine and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[(3-cyano-5-methoxyindol-1-yl)methyl]benzofuran-2-yl}thiazole.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4ca35fffe084b1ca2019fb6e9519012
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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