4-(Tri-n-butylstannyl)pyridine → HCID 67250916, compound

HRID 2427543Notes

Reaction equation

HRID 2427543 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)CCC.Br[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[C:26](=[O:30])[N:25]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)[CH2:24]2>C1(C)C=CC=CC=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>[CH3:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][N:25]2[CH2:24][C:23]3[C:27](=[CH:28][CH:29]=[C:21]([C:8]4[CH:7]=[CH:6][CH:11]=[CH:10][N:9]=4)[CH:22]=3)[C:26]2=[O:30])=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 57949631HCID 57949631, compound

Product 1

HCID 67250916HCID 67250916, compoundYield 169%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

4-Tributylstannanylpyridine (37 mg, 0.032 mmol), 5-bromo-2-(4-methyl-benzyl)-2,3-dihydro-isoindol-1-one (50.0 mg, 0.16 mmol) and Pd(PPh3)4 (37 mg, 0.032 mmol) were dissolved in anhydrous toluene (4 mL). The mixture was immersed in a 100° C. oil bath. After eighteen hours, the reaction was cooled and the solvent was removed under reduced pressure. The compound was purified by column chromatography (50% EtOAc/Hexanes) to provide the title compound as a brown solid (17.0 mg, 35%). 1H NMR (300 MHz, CDCl3): δ 8.72 (br s, 2H), 8.01 (d, 1H), 7.75 (dd, 1H), 7.62 (s, 1H), 7.53 (br s, 2H), 7.20 (q, 4H), 4.81 (s, 2H), 4.35 (s, 2H), 2.35 (s, 3H)

Workup

  1. customwas immersed in a 100° C.
  2. waitAfter eighteen hours
  3. temperaturethe reaction was cooled
  4. customthe solvent was removed under reduced pressure
  5. customThe compound was purified by column chromatography (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-2f2c5703585a4e009918ea797799f0d8
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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