5-Methyl-2-(tri-n-butylstannyl)pyridine → Methyl 3-(5-methylpyridin-2-yl)-5-(methylsulfonyl)benzoate

HRID 1845233Notes

Reaction equation

HRID 1845233 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[N:21][CH:22]=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>[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:21][CH:22]=1

Participants

5

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 22101072Methyl 3-bromo-5-methanesulfonylbenzoate

Product 1

HCID 58187970Methyl 3-(5-methylpyridin-2-yl)-5-(methylsulfonyl)benzoateYield 41.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 3-bromo-5-(methylsulfonyl)benzoate (1.0 g, 3.4 mmol), 5-methyl-2-(tributylstannyl)pyridine (1.2 mL, 3.5 mmol), tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol), and toluene (10 mL) under argon was subjected to microwave irradiation at 120° C. for 2 hours. The mixture was cooled to room temperature. The precipitate was collected by filtration and rinsed with hexane to afford the title compound as a light brown solid (432 mg). The filtrate was concentrated and the residue was purified via flash chromatography to afford another crop of the product as a light yellow solid (200 mg). 1H NMR (400 MHz, CDCl3): 8.91 (t, J=1.4 Hz, 1H), 8.80 (d, J=1.7 Hz, 1H), 8.61 (s, 1H), 8.58 (d, J=0.8 Hz, 1H), 7.76 (d, J=8.1 Hz, 1H), 7.65 (d, J=8.1 Hz, 1H), 4.00 (s, 3H), 3.15 (s, 3H), 2.42 (s, 3H).

Workup

  1. customirradiation at 120° C. for 2 hours
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with hexane

Sources & evidence

ORD record
ord-37fe0622ebed42d69269f569677e1408
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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