Iodoethane → HCID 56598655, compound

HRID 72655Notes

Reaction equation

HRID 72655 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][C:8]([CH2:15][S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])(=[O:18])=[O:17])=[CH:7][N:6]=1.I[CH2:34][CH3:35]>C1COCC1>[CH2:34]([N:11]([C:10]1[C:5]([O:4][CH3:3])=[N:6][CH:7]=[C:8]([CH2:15][S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])(=[O:18])=[O:17])[CH:9]=1)[C:12](=[O:14])[CH3:13])[CH3:35]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86690903(E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)acetamide

Product 1

HCID 56598655HCID 56598655, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.6 mg, 0.025 mmol) was added into the solution of (E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)acetamide (10 mg, 0.023 mmol) in dry THF (5 mL). The mixture was stirred at room temperature for 45 min. Iodoethane (15 μL, 0.05 mmol) was added dropwise into the mixture and stirred at room temperature for another 2 h. After evaporated to dryness, the residue was diluted with H2O (10 mL) and extracted (2×20 mL CH2Cl2). The combined extracts were extracted with sat. Na2CO3, washed with brine, dried on MgSO4, and filtered. The residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:1, v/v) to afford pure product as a white powder (8 mg, 75%). 1H-NMR (CDCl3): δ 1.02 (t, 3H, J=7.2 Hz, CH3), 1.74 (s, 3H, CH3), 3.42 (m, 2H, CH2), 3.86 (s, 6H, 2×OCH3), 3.87 (s, 3H, OCH3), 3.99 (s, 3H, OCH3), 4.23 (s, 2H, CH2), 6.10 (s, 2H, Ph-H), 7.07 (d, 1H, J=15.6 Hz, CH), 7.05 (d, 1H, J=2.0 Hz, Py-H), 7.77 (d, 1H, J=15.6 Hz, CH), 8.15 (d, 1H, J=2.0 Hz, Py-H); HR-MS (ESI+) m/z: 465.1762 [M+H]+, C22H28N2O7S, requires 464.1617.

Workup

  1. stirringstirred at room temperature for another 2 h
  2. customAfter evaporated to dryness
  3. additionthe residue was diluted with H2O (10 mL)
  4. extractionextracted (2×20 mL CH2Cl2)
  5. extractionThe combined extracts were extracted with sat. Na2CO3
  6. washwashed with brine
  7. customdried on MgSO4
  8. filtrationfiltered
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with PE/EtOAc (1:1

Sources & evidence

ORD record
ord-8722af966ee645ff8819628d69696677
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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