Selectfluor → 4-[2-(2,2-Dimethyl-5-oxopyrrolidin-1-yl)-5-fluoro-1,3-thiazol-4-yl]benzonitrile

HRID 1436434Notes

Reaction equation

HRID 1436434 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[N:12]=1.[B-](F)(F)(F)[F:23].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[C:8]1[S:9][C:10]([F:23])=[C:11]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[N:12]=1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 689027704-[2-(2,2-Dimethyl-5-oxopyrrolidin-1-yl)-1,3-thiazol-4-yl]benzonitrile

Product 1

HCID 250071034-[2-(2,2-Dimethyl-5-oxopyrrolidin-1-yl)-5-fluoro-1,3-thiazol-4-yl]benzonitrileYield 32%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-(2,2-Dimethyl-5-oxopyrrolidin-1-yl)-1,3-thiazol-4-yl]benzonitrile (0.50 g, 1.7 mmol), prepared in step 2 of Example 88, was dissolved in acetonitrile (16 mL) and the Selectfluor® reagent (0.65 g, 1.9 mmol) was added. The mixture was stirred for 16 h, diluted with ethyl acetate, washed with H2O, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone/hexane) afforded the title compound (0.17 g, 32%) as colorless crystals. HRMS: calcd for C16H14FN3OS+H+, 316.09144; found (ESI-FT/MS, [M+H]1+), 316.0916; Analytical HPLC purity 100% at 210-370 nm, 10.6 min; 98.4% at 296 nm, 10.6 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a27f94ae2b0e4bd6888a9ec829890b5b
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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