Methyl iodide → HCID 59506525, compound

HRID 1798894Notes

Reaction equation

HRID 1798894 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:18]3[C:19]4[C:11](=[N:12][NH:13][C:14]=4[N:15]=[C:16]([S:20][CH3:21])[N:17]=3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[C:24]([O-])([O-])=O.[Cs+].[Cs+].CI.C(OCC)(=O)C>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:18]3[C:19]4[C:11](=[N:12][N:13]([CH3:24])[C:14]=4[N:15]=[C:16]([S:20][CH3:21])[N:17]=3)[CH2:10][CH2:9]2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178490775HCID 178490775, compound

Product 1

HCID 59506525HCID 59506525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-methoxybenzyl)-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene (3.10 g, 9.48 mmol) in DMF (120 mL) was added Cs2CO3 (15.4 g, 47.43 mmol) and MeI (1.76 mL, 28.45 mmol). The mixture was stirred at room temperature for 16 h. Ethyl acetate (250 mL) and water (150 mL) was added. The EtOAc layer was separated, washed with aqueous NaCl (3×150 mL), dried over Na2SO4, filtered and concentrated. The obtained residue was purified by flash silica gel chromatography (eluent: 50% then 66% EtOAc in hexane). Compound 5-(4-methoxybenzyl)-1-methyl-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene compound 130 was obtained as a white solid (2.12 g, 95%). M.p. 105-108° C.; 1H NMR (CDCl3, 400 MHz) 6 7.25 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 4.77 (s, 2H), 3.92 (s, 3H), 3.79 (s, 3H), 3.54 (t, J=6.8 Hz, 2H), 3.04 (t, J=6.8 Hz, 2H), 2.61 (s, 3H). LC-Mass (m/e): 342.48 (M+1).

Workup

  1. customThe EtOAc layer was separated
  2. washwashed with aqueous NaCl (3×150 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained residue was purified by flash silica gel chromatography (eluent

Sources & evidence

ORD record
ord-716b1ef4a5b54122be889242599b5dca
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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