Water → 1-(3-bromophenyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one

HRID 571070Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([OH:14])[C:11](=[O:15])[CH:10]=[C:9]2[CH2:16][OH:17])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][CH:27]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([O:14][CH2:32][C:29]3[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=3)[C:11](=[O:15])[CH:10]=[C:9]2[CH2:16][OH:17])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1-(3-bromo-phenyl)-5-hydroxy-2-hydroxymethyl-1H-pyridin-4-one and K2CO3 (5.17 g, 37.5 mmol) in 50 mL of DMF was added 2.35 g of PMBCl (15 mmol) dropwise, and the reaction mixture was stirred at 80° C. for 3 h. After cooling to room temperature, the mixture was poured into 200 mL of water and extracted with EtOAc (50 mL) three times. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. Most of the volatiles were removed in vacuo and the resulting solid was collected and washed with EtOAc to obtain 1-(3-bromophenyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one. 1H NMR (400 MHz, DMSO-d6): δ 7.75 (d, J=8.0 Hz, 2H), 7.49 (d, J=4.0 Hz, 2H), 7.46 (s, 1H), 7.31 (d, J=7.6 Hz, 2H), 6.92 (d, J=7.6 Hz, 2H), 6.32 (s, 1H), 5.46 (s, 1H), 4.86 (s, 2H), 3.74 (s, 3H). ESI (M+H)+ 415.9/417.9

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (50 mL) three times
washThe combined organic layers were washed with water, brine
dry with materialdried over anhydrous MgSO4
customMost of the volatiles were removed in vacuo
customthe resulting solid was collected
washwashed with EtOAc

Sources & evidence

ORD record: ord-4f953ab4f82f482da4caa88d856b5261
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024032B2

Reaction notes

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