3-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine → HCID 15480241, compound

HRID 1780300Notes

Reaction equation

HRID 1780300 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])[CH:5]=[N:6][CH:7]=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>[N:6]1[CH:7]=[CH:2][CH:3]=[C:4]([C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[CH3:15])[CH:5]=[N:6][CH:7]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

Product 1

HCID 15480241HCID 15480241, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (272 mg, 1.0 mmol) in toluene (10.0 mL) was added 3-pyridinyltributyltin (442 mg, 1.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol). After being refluxed overnight, the resulting mixture was cooled to room temperature. Solvent was removed, and the residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford an oil (127 mg, 48%). MS (CI/NH3) m/z 270 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.70-1.93 (m, 3H), 2.00-2.12 (m, 1H), 2.28-2.39 (m, 1H), 2.52 (s, 3H), 2.67-2.76 (m, 1H), 3.11-3.18 (m, 1H), 3.98-4.13 (m, 2tt), 7.38-7.44 (m, 2H), 7.86-7.92 (m, 1H0, 8.37 (d, J=3.0 Hz, 1H), 8.46 (d, J=2.1 Hz, 1H), 8.67 (dd, J=6.0 Hz, J=1.8 Hz, 1H), 8.84 (d, J=2.1 Hz, 1H).

Workup

  1. temperatureAfter being refluxed overnight
  2. customSolvent was removed
  3. customthe residue was chromatographed on a silica gel column
  4. washeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

Sources & evidence

ORD record
ord-ced87e675ed7489c800811500c13562b
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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