Toluene → 2-(Benzyloxy)-6-(pyrrolidin-1-yl)pyridine

HRID 1360022Notes

Reaction equation

HRID 1360022 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 31268PyrrolidineHCID 8174752-Benzyloxy-6-bromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 669701082-(Benzyloxy)-6-(pyrrolidin-1-yl)pyridineYield 92.4%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a dried microwave reactor into which an argon gas was introduced, 526 mg (2.0 mmol) of 2-(benzyloxy)-6-bromopyridine, 200 μl (2.4 mmol) of pyrrolidine, 283 mg (2.8 mmol) of sodium t-butoxide, 9 mg (0.005 mmol) of tris(dibenzylideneacetone)dipalladium(O) (0.5 mol % of Pd), 19 mg (0.015 mmol, 1.5 mol %) of (±)-BINAP and 3 ml of toluene were placed, followed by stirring and reacting the mixture using microwave at 120° C. for 10 min. The reaction mixture was diluted with 20 ml of ethyl acetate, filtered through Cellite, and kept under a reduced pressure to remove the solvent. The residue was subjected to column chromatography using 10% ethyl acetate/hexane as an eluent to obtain 470 mg (yield 92%) of 2-(benzyloxy)-6-(pyrrolidin-1-yl)pyridine.

Workup

  1. additionIn a dried microwave reactor into which an argon gas was introduced
  2. customat 120° C.
  3. customfor 10 min
  4. filtrationfiltered through Cellite
  5. customto remove the solvent

Sources & evidence

ORD record
ord-f8aed5c7fff54172af91d4331e760ed4
Source dataset
uspto-grants-2011_02
Patent number
US07879835B2

Reaction notes

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