Aniline → HCID 57833590, compound

HRID 730072Notes

Reaction equation

HRID 730072 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][CH:23]=[C:22](OS(C(F)(F)F)(=O)=O)[C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4].[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Pd].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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[F:35][C:2]([F:36])([F:1])[C:3]([N:5]1[CH:6]2[CH2:12][CH2:11][CH:10]1[CH2:9][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:7]2)=[O:4]

Participants

8

Reactant 3

HCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 57833591HCID 57833591, compound

Product 1

HCID 57833590HCID 57833590, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of trifluoromethanesulfonic acid 9-[8-(2,2,2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-4-yl ester in toluene (0.1 to 2 M solution) may be treated with a catalytic amount of a palladium catalyst such as Pd2(dba)3 (0.01 to 0.1 equiv), DPPF (0.1 to 0.3 equiv), aniline (2 to 5 equiv), sodium tert-butoxide (1.2 to 2 equiv) under an argon atmosphere. The mixture may be heated to 80° C. for a period of 1 to 10 hr. After filtration and removal of the solvent via evaporation, the residue may be taken up in a halogenated solvent such as methylene chloride, and the solution may be washed with water, dried over a suitable drying agent such as magnesium sulfate, filtered, and concentrated. The residue may be purified via column chromatography to yield Compound 1d.

Workup

  1. filtrationAfter filtration and removal of the solvent
  2. customvia evaporation
  3. washthe solution may be washed with water
  4. dry with materialdried over a suitable drying agent such as magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue may be purified via column chromatography

Sources & evidence

ORD record
ord-1cf2344ba82049739874f1880f890849
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

Loading…