2-(Tributylstannyl)pyridine → HCID 18325026, compound

HRID 1250910Notes

Reaction equation

HRID 1250910 reaction equation
Br[C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C([Sn](CCCC)(CCCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)CCC>C(O)C.C(OCC)(=O)C.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>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:3]2[O:4][C:5]3[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=3[C:7](=[O:8])[C:2]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

6

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 10643413HCID 10643413, compound

Product 1

HCID 18325026HCID 18325026, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromo-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one (0.5 g, 1.32 mmol) from Example 22, Step 2 and 2-tributylstannylpyridine(0.58 g, 1.58 mmol) and tetrakis(triphenylphosphine)palladium(0.15 g, 0.13 mmol) in N-methyl-2-pyrrolidine(50 ml) and ethanol(1 ml) was heated at a temperature of 100° C. for 24 hours. Then the mixture was cooled to room temperature and diluted with ethyl acetate and filtered through a pad of celite. The mixture was washed with 5% aqueous KF, dried and concentrated. The residue was subjected to flash chromatography to yield the title compound as a pale yellow solid(0.27 g).

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe mixture was washed with 5% aqueous KF
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e658d09da76847f4affb1cec08c979d0
Source dataset
uspto-grants-2002_01
Patent number
US06340694B1

Reaction notes

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