4-Chlorophenyl Isocyanate → 1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-Chloro-phenyl)-urea

Participants

Role	Name	HCID	Charge
Reactant	4-Chlorophenyl Isocyanate	HCID 7693	—
Reactant	3-(4-Bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyaniline	HCID 11572741	—
Solvent	Dichloromethane	HCID 6344	—
Product	1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-Chloro-phenyl)-urea	HCID 11247569	84.8%

Reaction Steps

3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.260 g, 0.92 mmol) was treated with 4-chlorophenyl isocyanate (0.144 g, 0.92 mmol, 1.0 equiv.) in CH2Cl2 (5 mL), in a similar manner as described in Example 1.2 to afford Compound 1 (0.340 g, 0.78 mmol, 84%) as a white solid. LCMS m/z (%)=435 (M+H79Br35Cl, 77), 437 (M+H81Br35Cl, 100), 439 (M+H81Br37Cl, 25). 1H NMR (400 MHz, CDCl3) δ: 7.56 (s, 1H), 7.44 (dd, J=2.7, 8.9 Hz, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.29 (d, J=9.0 Hz, 1H), 7.19 (d, J=2.7 Hz, 1H), 6.59 (s, 1H), 6.47 (s, 1H), 3.84 (s, 3H), 3.74 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08754238B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-993bdac47a774e9398fc1fca2fd7e833
Source note	uspto-grants-2014_06