Cesium carbonate → Trifluoroacetic acid

HRID 1887675Notes

Reaction equation

HRID 1887675 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1.[CH3:23][O:24][C:25]1[CH:31]=[C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[CH:29]=[CH:28][C:26]=1[NH2:27].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:85](=[O:88])([O-])[O-:86].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:85]([OH:86])([C:19]([F:22])([F:21])[F:20])=[O:88].[CH3:23][O:24][C:25]1[CH:31]=[C:30]([N:32]2[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]2)[CH:29]=[CH:28][C:26]=1[NH:27][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 201362532-Methoxy-4-(4-methylpiperazin-1-yl)anilineHCID 566553282-[2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino]-N-methylbenzamide

Product 2

HCID 6422Trifluoroacetic acidHCID 250740802-(2-(2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Method C was applied to a mixture of 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (30 mg, 0.091 mmol), 2-methoxy-4-(4-methylpiperazin-1-yl)aniline (40 mg, 0.18 mmol), Pd2(dba)3 (11 mg, 0.012 mmol), rac-BINAP (12 mg, 0.019 mmol) and cesium carbonate (75 mg, 0.23 mmol) in dioxane (3 ml). The bis-TFA salt of the title compound was obtained as a pale yellow solid.

Sources & evidence

ORD record
ord-984228858774457e951f5c25e53c0ad3
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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