HCID 67050111, compound → HCID 67049806, compound

HRID 1875821Notes

Reaction equation

HRID 1875821 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]=2)=[C:6]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH:7]=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]=2)=[C:6]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 67050111HCID 67050111, compound

Product 1

HCID 67049806HCID 67049806, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-[5-chloro-2-(1-cyclohexylmethyl-1H-benzoimidazol-2-yl)-phenylethynyl]-benzonitrile (0.27 g, 0.6 mmol) in methanol was added 10% palladium on carbon and stirred for 16 h at 25° C. under hydrogen balloon pressure. The reaction mixture was filtered through a bed of celite and evaporated under reduced pressure. The residue was purified by column chromatography over silica gel (10-20% ethyl acetate/n-hexane) to yield the compound as an off-white powder (23%). MS (Turbo Spray): m/z=454.4 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel (10-20% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-05cc56150ba24be2af5d87546b4dda1f
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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