Tributylvinyltin → HCID 86673045, compound

HRID 1853278Notes

Reaction equation

HRID 1853278 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].[CH2:28]([Sn](CCCC)(CCCC)C=C)[CH2:29]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:28]=[CH2:29])[CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 86673027HCID 86673027, compound

Product 1

HCID 86673045HCID 86673045, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube was degassed with argon for 15 min. a solution of 6-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (100 mg, 0.236 mmol) in toluene. Tributyl(vinyl)tin (76 μl, 0.26 mmol) and tetrakis(triphenylphosphine)palladium (13 mg, 0.012 mmol) were added degassing was continued for 5 min. The tube was sealed and heated at 120° C. for 8 hours. The mixture was filtered, concentrated and purified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 0-10%) to yield 2-isoquinolin-3-yl-6-(vinyl)-chromen-4-one O-tert-butyl oxime (84 mg, 96%).

Workup

  1. customdegassing
  2. customThe tube was sealed
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. custompurified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 0-10%)

Sources & evidence

ORD record
ord-ceafa2db3a4a48f48abfa30492680163
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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