2-(Tributylstannyl)pyridine → HCID 10203901, compound

HRID 2415395Notes

Reaction equation

HRID 2415395 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:20][CH2:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]=3[CH:9]2[C:21]2[CH:22]=[CH:23][C:24]3[O:28][CH2:27][CH2:26][C:25]=3[CH:29]=2)=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)CCC>O1CCOCC1.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>[N:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:20][CH2:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]=3[CH:9]2[C:21]2[CH:22]=[CH:23][C:24]3[O:28][CH2:27][CH2:26][C:25]=3[CH:29]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 11328288HCID 11328288, compound

Product 1

HCID 10203901HCID 10203901, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The product from step A above (0.4 g, 0.896 mmol), 2-tributylstannanyl-pyridine (0.8 g, 2.17 mmol) and Pd(PPh3)4 (0.12 g, 0.104 mmol) were stirred in 1,4-dioxane (5 mL) at 88° C. for 24 h. The reaction mixture was filtered through a plug of Celite with CH2Cl2 and then concentrated to a small volume. Preparative TLC (3:7 ethyl acetate/heaxne; then 5% CH3OH/CH2Cl2) yielded the product as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite with CH2Cl2
  2. concentrationconcentrated to a small volume

Sources & evidence

ORD record
ord-bb1173b395de4095b0922005b3ab44a2
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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