Stannane, tributyl(1-ethoxyethenyl)- → 6-Chloro-1-(1-ethoxyvinyl) phthalazine

HRID 422569Notes

Reaction equation

HRID 422569 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC>CN(C=O)C.[Cu]I>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([C:18]([O:20][CH2:21][CH3:22])=[CH2:19])=[N:3][N:4]=[CH:5]2

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 143223331,6-Dichlorophthalazine

Product 1

HCID 666750006-Chloro-1-(1-ethoxyvinyl) phthalazine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a glass tube, a mixture of 1,6-dichlorophthalazine (1.18 g, 5.93 mmol) in 7.0 mL of DMF was treated with copper(I) iodide (113 mg, 0.59 mmol), tetrakistriphenylphosphine palladium (343 mg, 0.29 mmol) followed by tributyl(1-ethoxyvinyl)stannane (2.10 mL, 6.23 mmol). The glass tube was sealed and heated at 100° C. for 25 min in a microwave. The mixture was loaded on a silica gel column, eluting with 50-100% EtOAc in Hexanes, to provide 6-chloro-1-(1-ethoxyvinyl) phthalazine as a brown oil. MS (ESI, pos. ion) m/z: 235.1 (M+1).

Workup

  1. customThe glass tube was sealed
  2. washeluting with 50-100% EtOAc in Hexanes

Sources & evidence

ORD record
ord-22362c8564c7439db906b0c3c03831f4
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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