Tributylamine → HCID 18467547, compound

HRID 2229460Notes

Reaction equation

HRID 2229460 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22](I)[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19].[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](I)I.CC(C)=O.CN(C)C=O>[Cl:1][C:2]1[CH:23]=[C:22]([C:32]#[C:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19]

Participants

9

Reactant 4

HCID 7622TributylamineHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 22508742HCID 22508742, compound

Product 1

HCID 18467547HCID 18467547, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2-chloro-4-iodobenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (0.91 g), phenylacetylene (1.02 g), palladium acetate (II) (0.045 g), triphenylphosphine (0.105 g), tri n-butylamin (1.12 g), copper iodide (I) (0.038 g), and N,N-dimethylformamide (5 ml) was stirred for 1 hour at 70° C. and for 30 minutes at 100° C. After cooling the reaction solution, acetone was added thereto and the solution was filtrated with celite. The filtrate was concentrated and the resulting residue was dissolved in ethyl acetate followed by washing with 1N hydrochloric acid and a 10% aqueous solution of sodium hydroxide. The organic layer was dried and concentrated to obtain crude 1-(2-chloro-4-(phenylethynyl) benzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole. This product was immediately subjected to the next step.

Workup

  1. additionwas added
  2. filtrationthe solution was filtrated with celite
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe resulting residue was dissolved in ethyl acetate
  5. washby washing with 1N hydrochloric acid
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-50e011a5aa96491a82a30ae912a9de24
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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