Benzyl Bromide → HCID 118021937, compound

HRID 575788Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([CH3:20])[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:18][N:16]1[CH:17]=[C:12]([C:4]2[CH:3]=[C:2]([O:1][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=2)[CH:13]=[C:14]([CH3:20])[C:15]1=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A capped mixture of 5-(3-hydroxy-5-methylsulfonylphenyl)-1,3-dimethylpyridin-2-one (25 mg, 0.085 mmol), benzyl bromide (20 mg, 0.12 mmol), and Na2CO3 (18 mg, 0.17 mmol) in DMF (600 uL) was heated to 80° C. for 90 min. The mixture was filtered and the filter cake was washed with ACN (500 uL), the filtrate was purified by prep-HPLC to afford the title compound (8 mg, 25%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.08-2.13 (m, 3H) 3.26-3.28 (m, 3H) 3.51-3.57 (m, 3H) 5.22-5.34 (m, 2H) 7.33-7.47 (m, 4H) 7.48-7.53 (m, 2H) 7.54-7.60 (m, 1H) 7.67-7.71 (m, 1H) 7.83-7.88 (m, 1H) 8.17-8.22 (m, 1H). LCMS (M+H)+=384.

Workup

filtrationThe mixture was filtered
washthe filter cake was washed with ACN (500 uL)
customthe filtrate was purified by prep-HPLC

Sources & evidence

ORD record: ord-b2d7c58f58e7472aae43582b231c7953
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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