Cesium carbonate → HCID 59443069, compound

HRID 1959111Notes

Reaction equation

HRID 1959111 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:16]=3)[O:11][C:10]([CH3:27])([CH3:26])[CH:9]=2)=[CH:4][CH:3]=1.[S:28]([NH2:32])([CH3:31])(=[O:30])=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([NH:32][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:15][CH:16]=3)[O:11][C:10]([CH3:26])([CH3:27])[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 72879MethanesulfonamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59443040HCID 59443040, compound

Product 1

HCID 59443069HCID 59443069, compoundYield 57.6%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of [4-(4-chlorophenyl)-2,2-dimethyl-2H-chromen-7-yl]trifluoromethanesulfonate (100 mg), mesylamine (27 mg), cesium carbonate (117 mg), tris(dibenzylideneacetone)dipalladium (10 mg, 10% wt), 9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthen (Xantphos, 20 mg, 20% wt) and dioxane (2 mL) was heated under reflux for 10 hours. The reaction mixture was filtered, the filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=100/1) to give the titled compound (50 mg) as a colorless powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-a99aa831b70846b28033f7d1f697ef17
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

Loading…