Tributylstannane → HCID 22008827, compound

HRID 2287349Notes

Reaction equation

HRID 2287349 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:3]=1[C:4]([N:6]1[CH:11]=[CH:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[CH3:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[CH:7]1[CH2:8][C:9](=[O:12])[CH2:10][CH2:11][N:6]1[C:4]2=[O:5]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 22008821HCID 22008821, compound

Product 1

HCID 22008827HCID 22008827, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1-(2-bromo-5-methylbenzoyl)-2,3-dihydro-4-pyridinone (1.19 g, 4.03 mmol), tri-n-butyltin hydride (1.14 ml, 4.24 mmol) and azobis(isobutyronitrile) (AIBN, 66 mg, 10 mol %) in toluene (40 ml) was heated at 95° C. for 2 h, cooled, evaporated and purified by flash column chromatography on silica eluting with 30% ethyl acetate in hexane to yield the title compound as a pale yellow oil (276 mg), MS (+EI) m /z 215 [M+ ].

Workup

  1. temperaturecooled
  2. customevaporated
  3. custompurified by flash column chromatography on silica eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0409962496384cc284e672506399a662
Source dataset
uspto-grants-2000_07
Patent number
US06083952

Reaction notes

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