3-Chloro-5-fluoroaniline → N-(3-chloro-5-fluoro-phenyl)-2-(2,2-difluoroethoxy)-5-nitro-nicotinamide

HRID 1846125Notes

Reaction equation

HRID 1846125 reaction equation
[F:1][CH:2]([F:17])[CH2:3][O:4][C:5]1[N:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:6]=1[C:7](Cl)=[O:8].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([F:26])[CH:25]=1)[NH2:22].CSC1C2C(=CC(Br)=CC=2Br)NC=1SC>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:7](=[O:8])[C:6]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[N:13][C:5]=2[O:4][CH2:3][CH:2]([F:17])[F:1])[CH:23]=[C:24]([F:26])[CH:25]=1

Participants

5

Reactant 3

HCID 27348383-Chloro-5-fluoroanilineHCID 141858534,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indoleHCID 584834192-(2,2-Difluoroethyl)oxy-5-nitro-nicotinic acid chloride

Product 1

HCID 58483304N-(3-chloro-5-fluoro-phenyl)-2-(2,2-difluoroethoxy)-5-nitro-nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared analogously to example 6c with 2-(2,2-difluoro-ethoxy)-5-nitro-nicotinic acid chloride (prepared analogously to 6b) (179 mg; 0.67 mmol); 3-chloro-5-fluoroaniline (98 mg; 0.67 mmol) and TEA (112 μL; 0.81 mmol) in 5 mL DCM. Yield: 230 mg (91%); MS: [m+H]+=376 (Cl isotope pattern); HPLC: Rt=2.35 min (Method MC-6)

Sources & evidence

ORD record
ord-74b038ca8b8e4d5aa60bd40f58ab07ea
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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