Triethylamine → HCID 23729191, compound

HRID 2405060Notes

Reaction equation

HRID 2405060 reaction equation
[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]2[NH:6][C:7]([C:9]([OH:17])([CH2:14][C:15]#[CH:16])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[Cl:20][C:19]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]([OH:17])([CH2:14][C:15]#[C:16][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 23729508HCID 23729508, compound

Product 1

HCID 23729191HCID 23729191, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(5,6-Dichloro-1H-benzoimidazol-2-yl)-1,1,1-trifluoro-pent-4-yn-2-ol (0.27 g; 0.83 mmol), iodobenzene (0.14 mL; 1.3 mmol), dichlorobis(triphenylphosphine)palladium (31.7 mg; 0.045 mmol), copper iodide (17.8 mg; 0.093 mmol) and triethylamine (0.25 mL; 1.8 mmol) were suspended in THF (5 mL) and the resulting mixture stirred vigorously overnight. The reaction mixture was then concentrated in vacuo and the resulting crude brown oil was purified by column chromatography (SiO2; 50% ether/CH2Cl2) to yield the title compound as an orange-yellow solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe resulting crude brown oil was purified by column chromatography (SiO2; 50% ether/CH2Cl2)

Sources & evidence

ORD record
ord-7e0c1d0dcd28481a9d9aa5b289445719
Source dataset
uspto-grants-2014_08
Patent number
US08802865B2

Reaction notes

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