Cesium carbonate → Trifluoroacetic acid

HRID 1887685Notes

Reaction equation

HRID 1887685 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][CH2:14][C:15]1[C:16]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:17][CH:18]=[CH:19][CH:20]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[C:69](=[O:72])([O-])[O-:70].[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:69]([OH:70])([C:9]([F:12])([F:11])[F:10])=[O:72].[Cl:1][C:2]1[CH:7]=[C:6]([NH:13][CH2:14][C:15]2[C:16]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:17][CH:18]=[CH:19][CH:20]=2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27737912-Chloro-4-iodo-5-(trifluoromethyl)pyridineHCID 45480403N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 58155054HCID 58155054, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

The mixture of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (1 eq.), N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide (1 eq.), Pd2(dba)3, xantphos and cesium carbonate in dioxane were heated at 80° C. for 12 h. The solvent was removed and the residue was purified by prep. HPLC (0.1% TFA in water/acetonitrile gradient) to yield the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-99ff95bb417f4e9ca1ab2c6b17cdafac
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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