Selectfluor → 5-Fluoro-2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide

HRID 222802Notes

Reaction equation

HRID 222802 reaction equation
[CH:1]1([C@H:5]([NH:13][C:14]([C:16]2[C:21]([CH3:22])=[CH:20][C:19](=[O:23])[N:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]=2[CH3:30])=[O:15])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1.[B-](F)(F)(F)[F:32].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[CH:1]1([C@H:5]([NH:13][C:14]([C:16]2[C:21]([CH3:22])=[C:20]([F:32])[C:19](=[O:23])[N:18]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:17]=2[CH3:30])=[O:15])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 583075042,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide

Product 1

HCID 532392295-Fluoro-2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amideYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid [(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-amide (9.91 mg, 0.0245 mmol and selectfluor (10.0 mg, 0.0282 mmol) in acetonitrile (0.1 mL) was sonicated for 3 hrs at 40° C. then allowed to stand for 3 days. It was quenched with water (3 ml) and extracted with ethyl acetate (3×1 mL). The combined organic solution was transferred to a preparative TLC plate (SiO2, 0.25 mm×20 cm×20 cm) and eluted with ethyl acetate to give the crude title product (4 mg, 19% yield). LC-MS (m/z) 423.2 (MH+); tR=1.44.

Workup

  1. customwas sonicated for 3 hrs at 40° C.
  2. customIt was quenched with water (3 ml)
  3. extractionextracted with ethyl acetate (3×1 mL)
  4. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-1037bf22bf5942f0a73a46fefb548d40
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Reaction notes

Loading…