3-Iodopyridine → 3-Isopropoxy-4-(3-pyridyl)-cyclobut-3-ene-1,2-dione

HRID 991783Notes

Reaction equation

HRID 991783 reaction equation
[CH:1]([O:4][C:5]1[C:6](=[O:23])[C:7](=[O:22])[C:8]=1[Sn](CCCC)(CCCC)CCCC)([CH3:3])[CH3:2].I[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1>>[CH:1]([O:4][C:5]1[C:6](=[O:23])[C:7](=[O:22])[C:8]=1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 707143-IodopyridineHCID 27366833-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione

Product 1

HCID 120516723-Isopropoxy-4-(3-pyridyl)-cyclobut-3-ene-1,2-dione

Procedure

In a manner similar to Example 9, Step 1, 3-isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione (1.90 g, 4.43 mmol), 3-iodopyridine (1.00 g, 4.87 mmol), benzylchlorobis(triphenylphosphine)palladium (II) (0.201 g, 0.267 mmol), and cuprous iodide (0.076 g, 0.399 mmol) were reacted together to give the title compound which was of sufficient purity to use in the next step: 1H NMR (DMSO-d6) δ9.07(m,1H), 8.75(m,1H), 8.20(br d,1H), 7.65(m,1H), 5.50(sept,1H), 1.50(d,6H).

Sources & evidence

ORD record
ord-0b15d182aac849f19a64e66bf10f9c63
Source dataset
uspto-grants-2002_10
Patent number
US06465523B1

Reaction notes

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