Pyridine → 1-[2-(4-chloromethylphenyl)-2-oxo-ethyl]-4-(4-fluoro-benzyloxy)-1H-pyridin-2-one

HRID 564102

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=3)=[O:16])[C:10](=[O:25])[CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:36])=O>C(Cl)Cl.O>[Cl:36][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][N:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][C:10]2=[O:25])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 1.20 g (3.27 mmol) 4-(4-fluoro-benzyloxy)-1-[2-(4-hydroxymethyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one (preparation 31.1) in 20 mL DCM is added 0.29 mL (3.59 mmol) pyridine and 0.26 mL (3.59 mmol) thionylchloride at 0° C. The reaction mixture is stirred 1 h at 0° C., is warmed to RT and is then diluted with water. The organic phase is washed with saturated aqueous KHSO4-solution and then with water, dried over MgSO4, filtered over charcoal and the solvent is evaporated.

Workup

temperatureis warmed to RT
washThe organic phase is washed with saturated aqueous KHSO4-solution
dry with materialwith water, dried over MgSO4
filtrationfiltered over charcoal
customthe solvent is evaporated

Sources & evidence

ORD record: ord-e661e0376b52405a962b4a9660afb778
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067590B2

Linked notes

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