HCID 15524951, compound → HCID 67157886, compound

HRID 548550Notes

Reaction equation

HRID 548550 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Br:16])[CH:3]=1.[CH3:17][O:18][C:19](=[O:32])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]#[CH:31])=[CH:24][CH:23]=1>CN(C=O)C.C(N(CC)CC)C.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>[CH3:17][O:18][C:19](=[O:32])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]#[C:31][C:2]2[CH:7]=[C:6]([C:8]#[C:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[C:4]([Br:16])[CH:3]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 2

HCID 15524951HCID 15524951, compound2×HCID 86627833HCID 86627833, compound

Product 1

HCID 67157886HCID 67157886, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1,3-dibromo-5-phenylethynyl-benzene (0.1 g, 0.3 mmol, intermediate 3), (4-prop-2-ynyloxy-phenoxy)-acetic acid methyl ester (66 mg, 0.3 mmol), Pd(PPh3)2Cl2 (10 mg, 0.015 mmol), CuI (16 mg, 0.008 mmol) in dry DMF (1.5 ml) and triethylamine (1.5 ml) was heated in a microwave own for 10 min at 70° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography to give {4-[3-(3-bromo-5-phenylethynyl-phenyl)-prop-2-ynyloxy]-phenoxy}-acetic acid methyl ester in 27 mg (20%) yield.

Workup

  1. filtrationThe reaction mixture was filtered through Decalite
  2. customthe filtrate was evaporated
  3. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-0e67cbd1d51c47a7b91fdfc0df8e04d4
Source dataset
uspto-grants-2011_05
Patent number
US07943612B2

Reaction notes

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