tert-Butyl 4-ethynylpiperidine-1-carboxylate → Tert-butyl 4-[(5-fluoro-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)ethynyl]piperidine-1-carboxylate

HRID 1750008Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 5-fluoro-7-iodo-6-methoxybenzofuran-3(2H)-one (0.0582 g, 0.184 mmol) in triethylamine (3 mL) was added with tert-butyl 4-ethynylpiperidine-1-carboxylate (0.0389 g, 0.184 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.0129 g, 0.0184 mmol) and copper(I) iodide (0.00350 g, 0.0184 mmol), and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-[(5-fluoro-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)ethynyl]piperidine-1-carboxylate (0.0502 g, 70%).

Workup

concentrationThe reaction mixture was concentrated
customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-ced6da69a6d94e1995de7551b558cdb5
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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