5-Methyl-2-(tri-n-butylstannyl)pyridine → HCID 58188298, compound

HRID 1845253Notes

Reaction equation

HRID 1845253 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([Sn](CCCC)(CCCC)CCCC)=[N:19][CH:20]=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.C1(C)C=CC=CC=1>[CH3:13][O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:18]2[CH:17]=[CH:16][C:15]([CH3:14])=[CH:20][N:19]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 15618226Methyl 3-bromo-5-methoxybenzoate

Product 1

HCID 58188298HCID 58188298, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 3-bromo-5-methoxybenzoate (0.1 g, 0.4 mmol), 5-methyl-2-(tributylstannyl)pyridine (0.1 mL, 0.3 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol) and toluene (4 mL) under argon was subjected to microwave irradiation at 120° C. for 2 hours. The mixture was cooled to room temperature and purified via flash chromatography to afford the desired product as a light yellow oil. LC-MS: 257.9 [M+1]+.

Workup

  1. customirradiation at 120° C. for 2 hours
  2. custompurified via flash chromatography

Sources & evidence

ORD record
ord-d2f0339f514b40569e092e96bdcfd8c2
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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