4-Ethynyl-1,1'-biphenyl → HCID 66706342, Verbindung

HRID 1470640

Reaktionsgleichung

Reaktionsgleichung von HRID 1470640
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6](I)[C:5]=1[NH2:11].[C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)#[CH:14]>C1COCC1.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:14]#[C:13][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[C:5]=1[NH2:11]

Komponenten

6

Edukt 2

HCID 344644-Ethynyl-1,1'-biphenylHCID 21258150methyl 2-amino-3-iodobenzoate

Produkt 1

HCID 66706342HCID 66706342, VerbindungAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-3-iodo-benzoic acid methyl ester (500 mg, 1.8 mmol), 4-ethynyl-biphenyl (416 mg, 2.3 mmol) in THF (20 mL), CuI (17 mg, 0.09 mmol), bis-(triphenylphosphine)-palladium (II)-chloride (64 mg, 0.09 mmol) and TEA (0.75 mL, 5.4 mmol) were added. This mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion, the reaction mass was filtered through celite, and the collected filtrate was diluted with ethyl acetate (30 mL), washed with water (2×20 mL) and the combined organic layer was separated and dried over sodium sulphate and concentrated under reduced pressure to obtain brown mass which was purified by column chromatography using 5% ethyl acetate in hexane as an eluent to obtain 450 mg of 2-amino-3-biphenyl-4-ylethynyl-benzoic acid methyl ester as a pale yellow coloured solid (76%).

Aufarbeitung

  1. filtrationAfter completion, the reaction mass was filtered through celite
  2. additionthe collected filtrate was diluted with ethyl acetate (30 mL)
  3. washwashed with water (2×20 mL)
  4. customthe combined organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain brown mass which
  8. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ec4b4a98675e4a7e8de6f7f7588ea4e5
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006454B2

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