N-Iodosuccinimide → HCID 59580869, compound

HRID 1803431Notes

Reaction equation

HRID 1803431 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:11][N:12]=2)[CH:5]=[N:6][CH:7]=1.[I:21]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[C:11]([I:21])[N:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 66645339HCID 66645339, compound

Product 1

HCID 59580869HCID 59580869, compoundYield 84.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 2-(5-fluoropyridin-3-yl)thiazol-5-ylcarbamate (1.50 g, 5.08 mmol) in acetonitrile (50 mL) at 0° C. was added N-iodosuccinimide (2.40 g, 10.67 mmol). The mixture was stirred at 0° C. for 5 min and diluted with ethyl acetate and water. The organic phase was separated and rinsed with brine, dried over MgSO4 and concentrated in vacuo to give a dark solid. This solid was passed through a bed of silica gel (100g) eluting with 10% ether in hexanes (600 mL) to give tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-ylcarbamate as a pale yellow solid (1.80 g, 84% yield): mp 148-149° C.; 1H NMR (300 MHz, CDCl3) δ 8.87 (t, J=1.5 Hz, 1H), 8.47 (d, J=2.7 Hz, 1H), 7.93 (ddd, J=9.0, 2.5, 1.9 Hz, 1H), 7.08 (s, 1H), 1.57 (s, 9H). ESIMS m/z 422.1 (M+1), 420.2 (M-1),

Workup

  1. customThe organic phase was separated
  2. washrinsed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a dark solid
  6. washeluting with 10% ether in hexanes (600 mL)

Sources & evidence

ORD record
ord-748839f85f19445d808626d490a9f523
Source dataset
uspto-grants-2013_01
Patent number
US08350044B2

Reaction notes

Loading…