4-Bromo-2-hydroxypyridine → 4-bromo-1-[(R)-tetrahydro-furan-3-yl]-1H-pyridin-2-one

HRID 1425966Notes

Reaction equation

HRID 1425966 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[O:9]1[CH2:13][CH2:12][C@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10]1>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([C@@H:11]2[CH2:12][CH2:13][O:9][CH2:10]2)[C:4](=[O:8])[CH:3]=1

Participants

3

Reactant 2

HCID 8171154-Bromo-2-hydroxypyridineHCID 13837326(S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

Product 1

HCID 585641904-bromo-1-[(R)-tetrahydro-furan-3-yl]-1H-pyridin-2-oneYield 18%

Procedure

The title compound was prepared from 4-bromo-1H-pyridin-2-one and (S)-toluene-4-sulfonic acid tetrahydrofuran-3-yl ester following a procedure analogous to that described for Intermediate 8. Yield: 18% of theory; LC (method 3): tR=2.18 min; Mass spectrum (ESI+): m/z=244/246 (Br) [M+H]+.

Sources & evidence

ORD record
ord-f0e89774ced3477dafca2fa9e0fbfefb
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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