Iodoethane → HCID 58938128, compound

HRID 2246447Notes

Reaction equation

HRID 2246447 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[C:13]([C:15]#[N:16])[C:12]3[N:17]=[CH:18][NH:19][C:11]=3[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:29][CH3:30]>C(#N)C.ClCCl.O>[CH2:29]([N:19]1[C:11]2[CH:10]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:20])([F:1])[F:21])[CH:4]=3)[N:14]=[C:13]([C:15]#[N:16])[C:12]=2[N:17]=[CH:18]1)[CH3:30]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 49862793HCID 49862793, compound

Product 1

HCID 58938128HCID 58938128, compoundYield 7.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (50 mg, 0.17 mmol) in acetonitrile (1 ml) was added cesium carbonate (62 mg, 0.19 mmol) and iodoethane (15 μl, 0.19 mmol). The resulting suspension was stirred at room temperature overnight. Reaction mixture was diluted with dichloromethane (5 ml) and water (5 ml) and filtered through a hydrophobic frit and concentrated in vacuo. Residual orange oil was triturated with ether (5 ml) and resulting precipitate was filtered and dried to give the title compound as a pale yellow solid (4 mg). 1H NMR (MeOD): δ 8.56 (s, 1H), 8.52 (s, 1H), 8.46 (s, 1H), 8.41 (d, 1H), 7.71-7.74 (m, 2H), 4.46-4,51 (q, 2H), 1.57-1.61 (t, 3H). MS m/z 317.0 (M+1).

Workup

  1. customReaction mixture
  2. filtrationfiltered through a hydrophobic frit
  3. concentrationconcentrated in vacuo
  4. customResidual orange oil was triturated with ether (5 ml)
  5. customresulting precipitate
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-4593c413ce7a43ffafb5bca6a7407c04
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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