Methyl iodide → HCID 68950348, compound

HRID 238978Notes

Reaction equation

HRID 238978 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21]4)=[CH:16][CH:15]=3)(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:35]I>C1COCC1>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[S:6][C:7]([S:10]([N:13]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:23]4)=[CH:16][CH:15]=3)[CH3:35])(=[O:11])=[O:12])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86636898HCID 86636898, compound

Product 1

HCID 68950348HCID 68950348, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-(4-(5-chloro-3-methylbenzo[b]thiophene-2-sulfonamido)phenyl)azetidine-1-carboxylate (216 mg, 0.44 mmol) was stirred in THF (5 ml) and NaH (25 mg, 0.53 mmol) was added. After stirring at r.t. for 15 min, methyl iodide (0.028 ml, 0.44 mmol) was added and stirring was continued for 116 h. The solution was concentrated in vacuo, dissolved in water (pH 11) and extracted with EtOAc. The organic extracts were dried (MgSO4), filtered and concentrated to give tert-butyl 3-(4-(5-chloro-N,3-dimethylbenzo[b]thiophene-2-sulfonamido)phenyl)azetidine-1-carboxylate (=starting compound methylated at the amido-N) (185 mg, 83%).

Workup

  1. stirringstirring
  2. waitwas continued for 116 h
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutiondissolved in water (pH 11)
  5. extractionextracted with EtOAc
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ef4f4730c7104f44844f70a7daee971d
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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