Iodoethane → HCID 69359516, compound

HRID 852657Notes

Reaction equation

HRID 852657 reaction equation
[O:1]=[S:2]1(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2.[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C=O)C>[O:21]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69358280HCID 69358280, compound

Product 1

HCID 69359516HCID 69359516, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-indole-6-carboxylate (D231) (180 mg, 0.58 mmol, 1 equiv) in DMF (3 ml) at room temperature was added NaH (60% dispersion in mineral oil, 24 mg, 0.6 mmol, 1 equiv) and the resulting mixture was stirred 15 min at this temperature. Ethyl iodide (64 μl, 0.8 mmol, 1.4 equiv) was added and the resulting solution was stirred for 1 h then concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel gave methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1-ethyl-1H-indole-6-carboxylate (B147) (110 mg, 51%) as a yellow solid which was used in the next step without further purification. [M+H]+=337.0, RT=2.82 min.

Workup

  1. stirringthe resulting solution was stirred for 1 h
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with a 2N aqueous HCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2c3e1d2abb59406cb2bafad6fa05e023
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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