2-(Tributylstannyl)pyridine → HCID 59631328, compound

HRID 1431286Notes

Reaction equation

HRID 1431286 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)CCC>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>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 8178242,4-dichloro-3-methylquinoline

Product 1

HCID 59631328HCID 59631328, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to Procedure E using 2,4-dichloro-3-methylquinoline (1.038 g, 4.9 mmol), 2-(tributylstannyl)pyridine (2.0 g, 5.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.28 g, 0.24 mmol) in toluene (10.00 mL) to afford product as an off-white solid upon purification by precipitation from EtOAc and chromatography on silica gel, eluting with EtOAc gradient in hexane. Mass Spectrum (ESI) m/e=255.1 (M+1).

Workup

  1. customPrepared
  2. customto afford product as an off-white solid
  3. customupon purification
  4. customby precipitation from EtOAc and chromatography on silica gel
  5. washeluting with EtOAc gradient in hexane

Sources & evidence

ORD record
ord-b11a6e65c02d4656affccd5c5edb3757
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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