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

HRID 2377415Notes

Reaction equation

HRID 2377415 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.Br[C:16]1[CH:17]=[C:18]2[C:23](=[C:24](CNC3CC3)[CH:25]=1)[O:22][C:21](C)(C)[CH2:20][C:19]2(C)C.[CH2:35](N(CC)CC)C.[C:42](OCC)(=[O:44])[CH3:43]>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>[CH2:42]([O:44][C:21](=[O:22])[C:20]([CH3:35])=[CH:19][C:18]1[CH:17]=[CH:16][C:25]([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:24][CH:23]=1)[CH3:43]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 211072186-Bromo-8-[(cyclopropyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman2×HCID 21107260Cyclopropyl-(3-ethynyl-benzyl)-methyl-amine2×

Product 1

HCID 690699743-(4-{3-[(Cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-2-methyl-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-benzyl)-methyl-amine (Intermediate 91, 0.1 g, 0.54 mmol), (E)-3-(4-iodo-phenyl)-2-methyl-acrylic acid ethyl ester (Reagent 7, 0.17 g, 0.54 mmol), triethyl amine (10 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 2-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.15 g, 75%). 1H NMR (300 MHz, CDCl3): δ 7.66-7.25 (m, 9H), 4.27(q, J=7.3 Hz, 2H), 3.65(s, 2H), 2.25(s, 3H), 2.13 (d, J=1.2 Hz, 3H), 1.75-1.65(m, 1H), 1.35(t, J=7.3 Hz, 3H), 0.50-0.40(m, 4H).

Sources & evidence

ORD record
ord-d76a519dba7444da9376ceaca7e7613a
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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