Sodium Iodide → HCID 59506433, compound

HRID 1798893Notes

Reaction equation

HRID 1798893 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([O-])([O-])=O.[Cs+].[Cs+].[CH:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[CH:32][CH:31]=1.[Na+].[I-]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:36]([N:13]1[C:14]2=[C:19]3[C:18](=[N:17][C:16]([S:20][CH3:21])=[N:15]2)[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=2)[CH2:9][CH2:10][C:11]3=[N:12]1)[C:33]1[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 178490775HCID 178490775, compound

Product 1

HCID 59506433HCID 59506433, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-methoxybenzyl)-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene (4.32 g, 13.22 mmol) in DMF (160 mL) was added Cs2CO3 (21.48 g, 66.11 mmol), BnBr (1.88 mL, 15.86 mmol) and NaI (0.5 g). 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 60% EtOAc in hexane). Compound 129, 1-benzyl-5-(4-methoxybenzyl)-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene was obtained as a pale yellow solid (2.15 g, 39%). M.p. 168-170° C.; 1H NMR (CDCl3, 400 MHz) δ 7.31 (m, 5H), 7.25 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 5.42 (s, 2H), 4.76 (s, 2H), 3.79 (s, 3H), 3.52 (t, J=6.4 Hz, 2H), 3.02 (t, J=6.4 Hz, 2H), 2.62 (s, 3H). LC-Mass (m/e): 418.57 (M+1) and compound 129a, 1-benzyl-6-(4-methoxybenzyl)-4-(methylthio)-1,6,7,8-tetrahydro-1,2,3,5,6-pentaazaacenaphthylene was obtained as a pale yellow solid (2.35 g, 42%). M.p.>50° C.; 1H NMR (CDCl3, 400 MHz) δ 7.29 (m, 5H), 7.22 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 5.35 (s, 2H), 4.71 (s, 2H), 3.78 (s, 3H), 3.47 (t, J=6.0 Hz, 2H), 2.81 (t, J=6.0 Hz, 2H), 2.61 (s, 3H). LC-Mass (m/e): 418.57 (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-85b66553b2c64b66b5886f506a1381af
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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