Hydrochloric Acid → 4-Tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazole

HRID 1604658Notes

Reaction equation

HRID 1604658 reaction equation
[H-].[Na+].[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)#[N:4].[C:15]([C:19]1[N:20]=[C:21]([C:24]2[O:25][C:26]3[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][C:27]=3[CH:28]=2)[S:22][CH:23]=1)([CH3:18])([CH3:17])[CH3:16].[I-].[K+].Cl>CN(C)C=O>[C:15]([C:19]1[N:20]=[C:21]([C:24]2[O:25][C:26]3[CH:32]=[CH:31][C:30]([CH2:33][N:7]4[C:8]5[C:13](=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=5)[C:5]([C:3]#[N:4])=[CH:6]4)=[CH:29][C:27]=3[CH:28]=2)[S:22][CH:23]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 19603727HCID 19603727, compoundHCID 196038046-Methyl-1H-indole-3-carbonitrile

Product 1

HCID 196038354-Tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazoleYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 30 mg) was added into a solution of 3-cyano-6-methylindole (73 mg) in N,N-dimethylformamide (2 ml) at room temperature. After 30 minutes, 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (150 mg) and small amount of potassium iodide were added to the solution. After being stirred continuously for 3 hours, the resulting mixture was poured into ice-water and the mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazole (0.2 g).

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
  5. customto give a syrup
  6. washeluted with a mixture of toluene and ethyl acetate
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd2af3e2cad249369c26969eeb886719
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…