HCID 9857685, compound → HCID 54218913, compound

HRID 2305151Notes

Reaction equation

HRID 2305151 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[N:11][C:12]([Cl:16])=[C:13](Br)[CH:14]=1>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>[Cl:16][C:12]1[N:11]=[CH:10][C:9]([O:8][CH2:7][C@@H:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[CH:14][C:13]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 9857685HCID 9857685, compound

Product 1

HCID 54218913HCID 54218913, compoundYield 220.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloropyridine (500 mg, 1.28 mmol) in toluene (10 mL) was added 3-pyridinyltributyltin (564 mg, 1.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.04 mmol). After being heated under reflux for 16 h, the resulting mixture was cooled to room temperature. Solvent was removed, and the residue was chromatographed (silica gel; EtOAc/hexane, 2:19 to 1:1) to afford an oil (428 mg, 86%): 1H NMR (CDCl3, 300 MHz) δ 1.45 (s, 9H), 1.94 (m, 1H), 1.98-2.10 (m, 2H), 3.31-3.45 (m, 2H), 3.88-4.30 (m, 4H), 7.22 (m, 1H), 7.40 (m, 1H), 7.83 (td, 1H, J=1.5, 9.0 Hz), 8.16 (d, 1H, J=3.0 Hz), 8.64-8.73 (m, 2H); MS (CI/NH3) m/z 390 (M+H)+.

Workup

  1. temperatureAfter being heated
  2. temperatureunder reflux for 16 h
  3. customSolvent was removed
  4. customthe residue was chromatographed (silica gel; EtOAc/hexane, 2:19 to 1:1)

Sources & evidence

ORD record
ord-6f3cddbebf01449781ca4e30cf09d06f
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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