Selectfluor → HCID 68903067, compound

HRID 1436386Notes

Reaction equation

HRID 1436386 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[CH3:22][C:23]1([CH3:42])[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:29]1[S:30][CH:31]=[C:32]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[N:33]=1>C(#N)C>[CH3:22][C:23]1([CH3:42])[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:29]1[S:30][C:31]([F:21])=[C:32]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[N:33]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 24738462HCID 24738462, compound

Product 1

HCID 68903067HCID 68903067, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The Selectfluor® reagent (2.042 g, 5.76 mmol) in 250 mL of acetonitrile was added under nitrogen dropwise to a solution of 4-[2-(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile (1.566 g, 5.23 mmol), prepared in Example 6, in 250 mL of acetonitrile at room temperature. After the addition, the reaction was stirred at room temperature overnight. The reaction was concentrated under reduced pressure to remove the acetonitrile. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed once with water, and the solvent removed under reduced pressure. Purification of the residue on a Horizon™ Flash Collector (the Biotage FLASH 25+™ cartridge) using a linear gradient of methylene chloride in hexane as the eluent gave the title compound (566.7 mg, 34%) as a white solid, mp 177-178° C.; MS (ESI) m/z 318 [M+H]+. Anal. Calcd for C15H12FN3O2S: C, 56.77; H, 3.81; N, 13.24. Found: C, 56.53; H, 3.91; N, 13.12.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customto remove the acetonitrile
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed once with water
  7. customthe solvent removed under reduced pressure
  8. customPurification of the residue on a Horizon™ Flash Collector (the Biotage FLASH 25+™ cartridge)

Sources & evidence

ORD record
ord-c9313b2138f94b9aa0361a693307b8d7
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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