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

HRID 843048

Reaction equation

HRID 843048 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) δ 9.07(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-37d625cb77d44354bfa368a910e16fc6
Source dataset
uspto-grants-2002_04
Patent number
US06376555B1

Linked notes

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