Methyl iodide → HCID 59864878, compound

HRID 2423303Notes

Reaction equation

HRID 2423303 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][C:31]([OH:33])=[O:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:12]2[N:13]=[C:14]([CH3:24])[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:11]=2[CH:10]=1.[C:34](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:12]2[N:13]=[C:14]([CH3:24])[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59864787HCID 59864787, compound

Product 1

HCID 59864878HCID 59864878, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Under an N2 atmosphere, 2-(3-Chloro-4-(2-methyl-6-nitro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-benzo[d]imidazol-5-yloxy)phenyl)acetic acid (0.376 g, 0.764 mmol) was dissolved in DMF (3 mL). Cesium carbonate (0.274 g, 0.841 mmol) was added and the reaction was stirred at room temperature for 5 min. Iodomethane (0.052 mL, 0.841 mmol) was added and the reaction was allowed to stir at room temperature for 16 h. The reaction was diluted with diethyl ether and washed with water. The layers were separated and the aqueous layer was washed with additional diethyl ether. The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting with 10% to 30% isopropanol in hexanes, afforded the title compound. LC-MS ESI (pos.) m/z: 506.0 (M+H).

Workup

  1. stirringto stir at room temperature for 16 h
  2. washwashed with water
  3. customThe layers were separated
  4. washthe aqueous layer was washed with additional diethyl ether
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washFlash column chromatography of the residue, eluting with 10% to 30% isopropanol in hexanes

Sources & evidence

ORD record
ord-14b26057783140c5b1ccb833abfc656c
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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