Potassium Hydroxide → 5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

HRID 1270010

Reaction equation

HRID 1270010 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[OH-].[K+].[OH:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 693532,5-DibromopyridineHCID 762881-Pyrrolidineethanol

Product 1

HCID 105881665-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,5-dibromopyridine ( 15.0 g, 63.3 mmol), powdered KOH (6.39 g, 114 mmol), 1-(2-hydroxyethyl)pyrrolidine (14.58 g, 126.6 mmol), and 18-crown-6 (300 mg, 1.14 mmol) in dry toluene (100 mL) was heated to 70° C. for 1 h. The solution was cooled to room temperature and water and EtOAc were added. The organic layer was washed with water and brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo. Short path distillation (153° C. @0.1 mmHg) provided the title compound as a colorless oil which solidified upon cooling (14.9 g, 87%). 1H NMR (250 MHz, CDCl3): δ 8.15 (d, J=2.4 Hz, 1H), 7.65 (dd, J=2.4, 8.4 Hz, 1H), 6.67 (d, J=8.4 Hz, 1H), 4.38 (t, J=5.8 Hz, 2H), 2.84 (t, J=5.8 Hz, 2H), 2.62 (m, 4H), 1.82 (m, 4H).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. distillationShort path distillation (153° C. @0.1 mmHg)

Sources & evidence

ORD record
ord-12d1c0f7b89c4774be1ebbf9970b62dd
Source dataset
uspto-grants-2007_04
Patent number
USRE039558E1

Linked notes

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