3-Methoxyaniline → 2-Fluoro-5-(3-fluorophenyl)-N-(3-methoxyphenyl)benzamide
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C([O-])([O-])=O.[K+].[K+]>O=S(Cl)Cl.C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([NH:23][C:22]1[CH:24]=[CH:25][CH:26]=[C:20]([O:19][CH3:18])[CH:21]=1)=[O:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 2-fluoro-5-(3-fluorophenyl)benzoic acid (intermediate III(a)) (500 mg, 2.10 mmol, 1.0 eq) in SOCl2 (5 mL) was heated at 65° C. under N2 for 1 h. The solution was then evaporated in vacuo and the remaining residue dissolved in CH2Cl2 and added dropwise to a mixture of 3-methoxyaniline (220 mg. 1.9 mmol, 0.9 eq) and K2CO3 (1.4 g, 10.1 mmol, 5.0 eq) in THF (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with water and the solution extracted with EtOAc. The combined organic extracts were washed with aqueous Na2CO3 and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a colourless oil (580 mg, 96%).
Workup
- customThe solution was then evaporated in vacuo
- dissolutionthe remaining residue dissolved in CH2Cl2
- temperatureto warm to room temperature
- customThe reaction was quenched with water
- extractionthe solution extracted with EtOAc
- washThe combined organic extracts were washed with aqueous Na2CO3 and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-57a0bea7f3b64da4a7bba7e85935a1bf
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249085B2
Reaction notes
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