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

HRID 1765802Notes

Reaction equation

HRID 1765802 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>[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

7

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 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 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)—(0.71 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-cbae67c7c8ed4291a65286210237f7ae
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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