Water → HCID 59580494, compound

HRID 533318Notes

Reaction equation

HRID 533318 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:11][N:12]=2)[CH:5]=[N:6][CH:7]=1.[B-](F)(F)(F)[F:29].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.O>C(#N)C.CN(C=O)C>[F:29][C:11]1[N:12]=[C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)[S:9][C:10]=1[N:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 962WaterHCID 2724933SelectfluorHCID 59580505HCID 59580505, compound

Product 1

HCID 59580494HCID 59580494, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a degassed solution of di(tert-butyl) 2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate (1.0 g, 2.53 mmol) in anhydrous acetonitrile (20 mL) and DMF (10 mL) was added F-TEDA (SELECTFLUOR™) (1.8 g, 5.06 mmol). The reaction mixture was stirred at ambient temperature for 7 days. Water was added to the reaction mixture and the target extracted with ethyl acetate (2×). The organic layer was dried over sodium sulfate, was filtered and was concentrated. The crude mixture was purified via silica gel chromatography (0-100% ethyl acetate/hexanes) to afford a beige solid (860 mg, 82%): mp 143-143° C.; 1H NMR (300 MHz, CDCl3) δ 8.87 (t, J=1.4 Hz, 1H), 8.54 (d, J=2.7 Hz, 1H), 7.91 (ddd, J=8.9, 2.7, 1.8 Hz, 1H), 1.48 (s, 18H); ESIMS m/z 414 (M+1).

Workup

  1. extractionthe target extracted with ethyl acetate (2×)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationwas filtered
  4. concentrationwas concentrated
  5. customThe crude mixture was purified via silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2d24448fbcfc4270b9e97ec7b7337c2a
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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