2-Iodopyridine → 2-(4-(Pyridin-2-yl)but-3-ynyl)isoindoline-1,3-dione

HRID 1189339Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22])[CH2:9][C:10]#[CH:11]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22]

Participants

Reactant 2

HCID 2211262-Iodopyridine

HCID 11171619N-(3-Butynyl)phthalimide

Product 1

HCID 116447912-(4-(Pyridin-2-yl)but-3-ynyl)isoindoline-1,3-dioneYield 45%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-iodopyridine (453 mg, 2.21 mmol) and 2-(but-3-ynyl)isoindoline-1,3-dione (400 mg, 2.01 mmol, Example 189(B)). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 70:30) to yield 250 mg (0.90 mmol, 45%) of 2-(4-(pyridin-2-yl)but-3-ynyl)isoindoline-1,3-dione as.

Workup

customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 70:30)

Sources & evidence

ORD record: ord-d82280b882394a20a014162ac90475b5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674106B2

Reaction notes

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