5-Methyl-2-(tri-n-butylstannyl)pyridine → Methyl 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoate

HRID 1845223Notes

Reaction equation

HRID 1845223 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([Sn](CCCC)(CCCC)CCCC)=[N:24][CH:25]=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>[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:24][CH:25]=1

Participants

4

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 58188186Methyl 3-bromo-5-(pyrrolidine-1-carbonyl)benzoate

Product 1

HCID 58188359Methyl 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-1-carbonyl)benzoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of methyl 3-bromo-5-(pyrrolidine-1-carbonyl)benzoate (1.2 g, 3.8 mmol), 5-methyl-2-(tributylstannyl)pyridine (0.90 mL, 2.6 mmol), tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.086 mmol) under argon was subjected to microwave irradiation at 120° C. for 2 hour. The mixture was cooled to room temperature and the precipitate was collected by filtration and rinsed with hexane to afford the title compound as a white solid. The filtrate was concentrated and purified via flash chromatography to afford another crop of the desired product. LC-MS: 325.1 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-37c69809e4cd4a258fd198adb5e404c5
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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