147539-53-5 → HCID 71278755, compound

HRID 1750011Notes

Reaction equation

I[C:2]1[C:10]2[O:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[CH3:14][C:15]([N:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)([C:17]#[CH:18])[CH3:16]>C(N(CC)CC)C.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.[Cu]I>[CH3:13][O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[CH2:8][O:9][C:10]=2[C:2]=1[C:18]#[C:17][C:15]([N:19]1[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]1)([CH3:16])[CH3:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 7-iodo-6-methoxybenzofuran-3(2H)-one (0.290 g, 1.00 mmol) synthesized in Example B46, Step 2, dichlorobis(triphenylphosphine)palladium(II) (0.0702 g, 0.100 mmol) and copper(I) iodide (0.0190 g, 0.100 mmol) in triethylamine (4 mL) was added with a solution of tert-butyl 4-(2-methylbut-3-yn-2-yl)piperazine-1-carboxylate (Journal of Medicinal Chemistry, Vol. 47, p. 2833, 2004, 0.252 g, 1.00 mmol) in triethylamine (4 mL), and the mixture was stirred at 50° C. for 7.5 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl 4-[4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)-2-methylbut-3-yn-2-yl]piperazine-1-carboxylate (0.126 g, 30%).

Workup

concentrationThe reaction mixture was concentrated
customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-2d49a55022b14c16882b18f8fc1c85a0
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

Loading…