Sodium Iodide → HCID 18378587, compound

HRID 2298814Notes

Reaction equation

HRID 2298814 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.[CH3:8][C:9]1[S:33][C:12]2[N:13]([C:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([O:31][CH3:32])[CH:22]=3)=[O:20])[CH2:14][CH2:15][CH2:16][CH:17](O)[C:11]=2[C:10]=1[CH3:34]>CCCCCC.C(#N)C.C(OCC)(=O)C>[CH3:8][C:9]1[S:33][C:12]2[N:13]([C:19]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([O:31][CH3:32])[CH:22]=3)=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][C:11]=2[C:10]=1[CH3:34]

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 18378554HCID 18378554, compound

Product 1

HCID 18378587HCID 18378587, compoundYield 78.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium iodide (462 mg), chlorotrimethylsilane (335 mg) and acetonitrile (0.2 ml) in hexane (0.5 ml) was cooled to 0° C. To the solution was added methyl 4-(2,3-dimethyl-4-hydroxy-5,6,7,8-tetrahydro-4H-thieno[2,3-b]azepin-8-yl)carbonyl-2-methoxybenzoate (200 mg) in acetonitrile (1.0 ml). The mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography (SiO2; 30 g, CHCl3) to give methyl 4-(2,3-dimethyl-5,6,7,8-tetrahydro-4H-thieno[2,3-b]azepin-8-yl)carbonyl-2-methoxybenzoate (150 mg).

Workup

  1. washwashed with aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by silica gel column chromatography (SiO2; 30 g, CHCl3)

Sources & evidence

ORD record
ord-f02fe0e8ef164c8db323c55b1c9f68bd
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

Loading…