HCID 58370136, compound → HCID 68840871, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1Br)=[O:9])([CH3:6])[CH3:5]>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:21])[C:4]([CH3:6])([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:16]#[C:15][CH2:14][CH2:13][C:12]1[CH:17]=[CH:18][CH:19]=[CH:10][CH:11]=1)=[O:9])[CH3:5]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
40 mg 2-[(1-bromo-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester and 0.8 mg bis(triphenylphosphine)palladium(II)chloride were placed in a reaction vial, which was evaporated and backfilled with argon three times. Via septum 18 mg of 4-phenyl-1-butyne, 180 μl diethylamine and 0.2 ml abs. DMF were added. In a microwave reactor the reaction was heated to 130° C. for 5 min. Then, water and ethyl acetate were added, the layers were separated, and the aqueous phase was extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate and concentrated. The resulting residue was purified by chromatography on silica (ethyl acetate/heptane) to yield 25 mg of 2-methyl-2-{[1-(4-phenyl-but-1-ynyl)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester.
Workup
- customwhich was evaporated
- additionDMF were added
- additionThen, water and ethyl acetate were added
- customthe layers were separated
- extractionthe aqueous phase was extracted with ethyl acetate twice
- dry with materialThe combined organic layers were dried over magnesium sulphate
- concentrationconcentrated
- customThe resulting residue was purified by chromatography on silica (ethyl acetate/heptane)
Sources & evidence
- ORD record
- ord-1a961a147c86461ab56027082f8a4416
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501981B2
Reaction notes
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