4-Fluoroaniline → (4-Fluoro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl-amine

HRID 1043660Notes

Reaction equation

HRID 1043660 reaction equation
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[CH:9][N:4]2[N:3]=1.[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>ClCCl>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2]2[S:6][C:5]3=[N:7][CH:8]=[CH:9][N:4]3[N:3]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 436679232-Bromoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 67335853(4-Fluoro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl-amineYield 10.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
135 °C

Procedure

A mixture of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (1.0 g, 4.90 mmol) and 4-fluoroaniline (1.86 mL, 19.60 mmol) was heated under microwave irradiation at 135° C. for 15 minutes. On cooling, the mixture was diluted with dichloromethane (10 mL) and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1:9). The residue obtained was treated with dichloromethane (5 mL) and filtered to give (4-fluoro-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl-amine as a beige solid (117 mg, 10% yield).

Workup

  1. temperatureOn cooling
  2. custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1:9)
  3. customThe residue obtained
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a6957e22a0ec4780a3af79f4d3d70ae7
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

Loading…