Isatin → HCID 22022453, compound

HRID 218105Notes

Reaction equation

HRID 218105 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].Br[CH2:15][C:16]1[C:17]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=2[S:19][CH:20]=1>O1CCOCC1>[Cl:25][C:23]1[CH:22]=[CH:21][C:18]2[S:19][CH:20]=[C:16]([CH2:15][N:1]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4](=[O:5])[C:2]3=[O:3])[C:17]=2[CH:24]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 24758Sodium hydrideHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiophene

Product 1

HCID 22022453HCID 22022453, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A solution of isatin (125 mg, 0.85 mmol) in anhydrous dioxane (10 mL) was added dropwise to a solution of sodium hydride (60% dispersion in mineral oil, 25 mg, 0.62 mmol) in anhydrous dioxane (10 mL) at 0° C. under argon. The mixture was allowed to stir for 5 minutes and then a solution of 3-(bromomethyl)-5-chlorobenzo[b]thiophene (267 mg, 1.02 mmol) in dioxane (10 mL) was added dropwise to the reaction mixture. The reaction mixture was heated at reflux under argon for 16 h and concentrated in vacuo. The crude material was purified by preparative TLC using 1:24 methanol in chloroform as the eluent, giving the desired product as a yellow solid (125 mg, 0.38 mmol, 45%). 1H NMR (400 MHz): δ 7.89 (s, 1H), 7.79 (d, J=8.5, 1H), 7.65 (d, J=7.5, 1H), 7.54 (t, J=8.0, 1H), 7.42 (s, 1H), 7.38. (d, J=8.5, 1H), 7.14 (t, J=7.5, 1H), 6.88 (d, J=7.8, 1H), 5.13 (s, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under argon for 16 h
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by preparative TLC

Sources & evidence

ORD record
ord-f3a9b62414e34e27907c4b7c74e74d70
Source dataset
uspto-grants-2012_06
Patent number
US08198313B2

Reaction notes

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