3-Bromopyridine → HCID 69052614, compound

HRID 227233Notes

Reaction equation

HRID 227233 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18])#[CH:9]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]#[C:9][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

4

Reactant 2

HCID 122863-BromopyridineHCID 50998820875768-16-4

Product 1

HCID 69052614HCID 69052614, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-bromopyridine (608 mg, 3.85 mmol), PdCl2(PPh3)2 (246 mg, 0.35 mmol), and Cu(1)I (733 mg, 3.85 mmol) was added TEA (10 mL) followed by 1-ethynyl-4-methyl-2-nitro-benzene (564 mg, 3.5 mmol). After stirring at 60° C. for 4 h, the reaction was filtered, and diluted with EtOAc (150 mL) and 10% Na2CO3 (150 mL). The organic layer was washed with brine, dried over MgSO4; filtered, and dried under reduced pressure. The material was purified using a Biotage 40M cartridge eluting with hexanes/EtOAc (7/3) to yield a light brown oil.

Workup

  1. filtrationthe reaction was filtered
  2. additiondiluted with EtOAc (150 mL) and 10% Na2CO3 (150 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customdried under reduced pressure
  7. customThe material was purified
  8. washeluting with hexanes/EtOAc (7/3)
  9. customto yield a light brown oil

Sources & evidence

ORD record
ord-d7640c7d74c2422388ac9c0660be5fa4
Source dataset
uspto-grants-2009_07
Patent number
US07560462B2

Reaction notes

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