4-Ethynyl-1,1'-biphenyl → 2-Amino-3-biphenyl-4-ylethynyl-benzoic acid methyl ester

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%).

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

ORD-Eintrag

ord-ec4b4a98675e4a7e8de6f7f7588ea4e5

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09006454B2