Triethylamine → (E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl ester

HRID 2377422Notes

Reaction equation

HRID 2377422 reaction equation
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:14]#[CH:15])[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.[CH2:16]([O:18][C:19](=[O:48])/[C:20](/C)=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25](C#CC2C=C(C3CC3)C3OC4(CC4)C(C)=C(C)C=3C=2)=[CH:24][CH:23]=1)[CH3:17].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>[CH2:16]([O:18][C:19](=[O:48])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([C:15]#[C:14][C:9]2[CH:8]=[C:7]([CH2:6][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])[CH:12]=[CH:11][C:10]=2[CH3:13])=[CH:24][CH:23]=1)[CH3:17]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21107259Cyclopropyl-(3-ethynyl-4-methylbenzyl)-methyl-amine2×HCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester2×

Product 1

HCID 57462494(E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl 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-4-methyl-benzyl)-methyl-amine (Intermediate 99, 0.095 g, 0.48 mmol), ethyl-4-iodo-cinnamate (Reagent 3, 0.144 g, 0.47 mmol), triethyl amine (13 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.071 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-20% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 82%).

Sources & evidence

ORD record
ord-361bcd538d0d43efb401f6cde8f57462
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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