Phenylacetylene → HCID 117915868, compound

HRID 923665Notes

Reaction equation

HRID 923665 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]([O:9][CH3:10])=[C:4](Br)[N:3]=1.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[CH:13]>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.C1COCC1>[Br:8][C:6]1[C:5]([O:9][CH3:10])=[C:4]([C:13]#[C:12][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=[C:2]([NH2:1])[CH:7]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 117903200HCID 117903200, compound

Product 1

HCID 117915868HCID 117915868, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dichlorobis(triphenylphosphine)palladium(II) (17 mg, 25 μmol) is added to a mixture of 2-amino-4,6-dibromo-5-methoxy-pyridine A1 (70 mg, 0.25 mmol), ethynylbenzene (55 μl, 0.50 mmol), copper(I) iodide (5 mg, 25 μmol) triethylamine (140 μl,1 mmol) and THF (1 ml) under argon atmosphere and is stirred at 50° C. for 1 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 35 mg (47%). HPLC-MS: tR=1.21 min (METHOD—1).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-5118fa3e9ecc4b3b9173480d5b25c0d2
Source dataset
uspto-grants-2016_03
Patent number
US09278978B2

Reaction notes

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