3-(Tributylstannyl)pyridine → HCID 54285809, compound

HRID 611593Notes

Reaction equation

HRID 611593 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[C:18](Br)[CH:19]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([Sn](CCCC)(CCCC)[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)CCC>C1(C)C=CC=CC=1.[Pd]>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH:19]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 34838483-(Tributylstannyl)pyridineHCID 18396230HCID 18396230, compound

Product 1

HCID 54285809HCID 54285809, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

The 2-(1-BOC-2-(S)-pyrrolidinyl)-6-bromofuro[3,2-b]pyridine (0.24g, 0.64 mmol) obtained from Example 46a above was dissolved in toluene (6 mL). Tributyl-3-pyridyltin (0.36 g, 1.3 mmol), palladium (O) tetrakis(triphenyl phosphine) (40 mg) was then added to the toluene solution and the resultant mixture was heated under reflux for 16 h. The desired product was extracted with CH2Cl2, dried over MgSO4 and filtered. Solvent was then removed under reduced pressure and the residue was chromatographed (silica gel: Hexane/EtOAc, 5:1 to EtOAc) to afford an oil (0.13 g, 56%). MS (CI/NH3) m/z: 366 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ 1.33, 1.55 (2s, 9H), 1.92-2.38 (m, 3H), 3.43-3.70 (m, 2H), 5.08 (m, 1H), 5.15 (m, 1H), 6.75 (brs, 1H), 7.43 (m, 1H), 7.86 (s, 1H), 7.93 (m, 1H), 8.66 (m, 1H), 8.72 (brs, 1H), 8.89 (s, 1H).

Workup

  1. temperatureunder reflux for 16 h
  2. extractionThe desired product was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customSolvent was then removed under reduced pressure
  6. customthe residue was chromatographed (silica gel: Hexane/EtOAc, 5:1 to EtOAc)

Sources & evidence

ORD record
ord-c2cae21c20fb489d855251d63e717ba9
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

Loading…