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

HRID 1869935Notes

Reaction equation

HRID 1869935 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-cfd3e8501ea24e5cb4f0bfddf7a77495
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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