3-(Trifluoromethyl)phenyl isocyanate → 1-(5-Bromopyridin-2-yl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 1446747Notes

Reaction equation

HRID 1446747 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13]([N:17]=[C:18]=[O:19])[CH:14]=[CH:15][CH:16]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([F:9])([F:20])[F:21])[CH:12]=2)=[O:19])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 706222-Amino-5-bromopyridine

Product 1

HCID 606503781-(5-Bromopyridin-2-yl)-3-(3-(trifluoromethyl)phenyl)ureaYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromopyridin-2-yl amine (1.190 g, 6.88 mmol, 1.0 eq.) in THF (20 mL), add 3-trifluoromethylphenyl isocyanate (0.96 mL, 6.88 mmol, 1.0 eq.) in a drop-wise manner at room temperature. Stir the reaction mixture at room temperature for 30 minutes. Filter the solid and wash with MeOH (2×10 mL). Dry the solid to afford 1.81 g (5.0 mmol, 73%) of the title compound. MS (ES), m/z 360, 362 (M+1).

Workup

  1. filtrationFilter the solid
  2. washwash with MeOH (2×10 mL)
  3. customDry the solid

Sources & evidence

ORD record
ord-bc742a9ac60145c5ae3820ec6fb8cdde
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…