5-Methyl-2-(tri-n-butylstannyl)pyridine → HCID 58188123, compound

HRID 1845249Notes

Reaction equation

HRID 1845249 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([O:19][C:20]([F:23])([F:22])[F:21])[CH:18]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:6].[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([Sn](CCCC)(CCCC)CCCC)=[N:29][CH:30]=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>[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([C:2]2[CH:3]=[C:4]([CH:16]=[C:17]([O:19][C:20]([F:23])([F:22])[F:21])[CH:18]=2)[C:5]([NH:7][CH2:8][C:9]2[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:6])=[N:29][CH:30]=1

Participants

5

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 58188114HCID 58188114, compound

Product 1

HCID 58188123HCID 58188123, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-bromo-N-((6-methylpyridin-3-yl)methyl)-5-(trifluoromethoxy)benzamide (60 mg, 0.15 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. LC-MS indicated strong peak of starting material. The mixture was degassed with nitrogen and re-applied to microwave irradiation at 120° C. for 2 hours. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified via preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH]) to afford the desired product as a white solid.

Workup

  1. customirradiation at 120° C. for 2 hours
  2. customThe mixture was degassed with nitrogen and re-applied
  3. customirradiation at 120° C. for 2 hours
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH])

Sources & evidence

ORD record
ord-60965c36ac2942a0832e71617fc437e4
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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