Sodium hydride → 5-bromo-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine

HRID 365828Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[H-].[Na+].[S:11]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[CH2:26][OH:27])([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>CN(C=O)C>[Br:8][C:6]1[CH:7]=[C:2]([O:27][CH2:26][C@@H:22]2[CH2:23][CH2:24][CH2:25][N:21]2[S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=2)(=[O:13])=[O:12])[CH:3]=[N:4][CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 3,5-dibromopyridine (1.5 g, 6.05 mmol) and 60% NaH (307 mg, 7.7 mmol) in DMF (6 mL) was added 1-tosyl-2-(S)-pyrrolidinemethanol (1.4 g, 5.5 mmol), and the reaction mixture was stirred for 4 hours at room temperature and 1 hour at 60° C. The DMF was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with EtOAc/hexane 6:1 to afford the title compound (1.2 g).

Workup

customThe DMF was removed under reduced pressure
customthe residue was chromatographed on a silica gel column
washeluting with EtOAc/hexane 6:1

Sources & evidence

ORD record: ord-13ff497395214ed6ab0f170a4b139570
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127386

Reaction notes

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