2-Fluoro-5-(trifluoromethyl)aniline → 6-((6,7-Bis(methoxy)-4-quinolinyl)oxy)-n-(2-fluoro-5-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

HRID 1925321Notes

Reaction equation

HRID 1925321 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([C:38](Cl)=[O:39])=[CH:33][CH:32]=[CH:31]2>CN(C1C=CN=CC=1)C.ClCCl>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([C:38]([NH:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[CH:5]=[CH:6][C:7]=1[F:8])=[O:39])=[CH:33][CH:32]=[CH:31]2

Participants

5

Reactant 2

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 248229436-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride

Product 1

HCID 598134076-((6,7-Bis(methoxy)-4-quinolinyl)oxy)-n-(2-fluoro-5-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Into a 16×100 mm vial was added 3-amino-4-fluorobenzotrifluoride (100 mg, 0.563 mmol), and dichloromethane (1 mL). To this was added 1.5 mL of a stock solution that is both 0.25M 6-(6,7-dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride and 0.5M DMAP in dichloromethane. Reactions was stirred 24 h at RT. The mixture loaded directly onto silica column. Purified using 0 to 100% EtOAc in hexane. Best fractions were pooled, concentrated under reduced pressure to afford the title compound as a yellow oil. MS (ESI, pos. ion) m/z: 537 (M+1). Mass Calc'd for C29H20F4N2O4: 536.47.

Workup

  1. customPurified
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12f8e5983ff546bbbdc2ad28f847f03b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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