Triethylamine → (E)-3-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}phenyl)-acrylic acid methyl ester

HRID 1869932Notes

Reaction equation

HRID 1869932 reaction equation
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[CH:14])[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.[CH2:15]([O:22][C:23](=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)C1C=CC=CC=1.C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[Cu]I.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>[CH3:15][O:22][C:23](=[O:33])/[CH:24]=[CH:25]/[C:26]1[CH:27]=[CH:28][C:29]([C:14]#[C:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])[CH:8]=2)=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21107260Cyclopropyl-(3-ethynyl-benzyl)-methyl-amine2×HCID 566275053-(4-Hydroxy-phenyl)-acrylic acid benzyl ester2×

Product 1

HCID 57987781(E)-3-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}phenyl)-acrylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure B and using cyclopropyl-(3-ethynyl-benzyl)-methyl-amine (Intermediate 91, 0.060 g, 0.32 mmol), methyl-4-iodo-cinnamate (Reagent 4, 0.093 g, 0.32 mmol), triethyl amine (8 mL), copper(I)iodide (0.015 g, 0.08 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.056 g, 0.08 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-15% ethyl acetate in hexane as the eluent, the title compound was obtained (0.11 g, 100%).

Sources & evidence

ORD record
ord-f57719075ec5465e9716cd9e01c30ecd
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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