Methyl iodide → HCID 68637269, compound

HRID 656807Notes

Reaction equation

HRID 656807 reaction equation
[CH:1]1([C:4]2[C:5]([N:31]3[CH2:35][CH2:34][NH:33][S:32]3(=[O:37])=[O:36])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([O:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[CH:14][CH:13]=4)=[C:9]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:8]=3[CH:30]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:40]I>CN(C=O)C>[CH:1]1([C:4]2[C:5]([N:31]3[CH2:35][CH2:34][N:33]([CH3:40])[S:32]3(=[O:36])=[O:37])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([O:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)=[CH:14][CH:13]=4)=[C:9]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:8]=3[CH:30]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68638142HCID 68638142, compound

Product 1

HCID 68637269HCID 68637269, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 62 (0.058 g, 0.11 mmol) and dry DMF (5 mL) was added sequentially NaH (5 mg, 0.12 mmol, 50% mineral oil dispersion) and MeI (0.08 mL, 0.14 mmol). The reaction mixture was stirred for 15 min then quenched with H2O and extracted with EtOAc/Et2O. The organic phase was washed sequentially with H2O and brine, dried (MgSO4), filtered and evaporated to afford 30 mg of ethyl 5-cyclopropyl-6-(5-methyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)-2-(4-phenoxy-phenyl)-benzofuran-3-carboxylate (64). Hydrolysis of the ethyl ester and conversion to the amide was carried out as previously described in steps 12 and 13 of example 3 to afford I-105.

Workup

  1. customthen quenched with H2O
  2. extractionextracted with EtOAc/Et2O
  3. washThe organic phase was washed sequentially with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1fa8eef95f034974a80ac395c27c4af3
Source dataset
uspto-grants-2011_12
Patent number
US08071797B2

Reaction notes

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