Cesium carbonate → HCID 22042246, compound

HRID 1790853Notes

Reaction equation

HRID 1790853 reaction equation
[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([N+:36]([O-:38])=[O:37])[CH:30]=1.C(=O)([O-])[O-].[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:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH:33][C:32]1[CH:34]=[CH:35][C:29]([O:28][CH3:27])=[CH:30][C:31]=1[N+:36]([O-:38])=[O:37])[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 667934-Methoxy-2-nitroanilineHCID 21020313HCID 21020313, compound

Product 1

HCID 22042246HCID 22042246, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Trifluoro-methanesulfonic acid 8-(tert-butyl-dimethyl-silanyloxy)-quinolin-2-yl ester B (9.81 g, 24.1 mmol) and 4-methoxy-2-nitroaniline (4.86 g, 28.9 mmol) were dissolved in 100 mL of dioxane under an atmosphere of dry N2. To this solution was added (11.0 g, 33.7 mmol) cesium carbonate (Cs2CO3), (900 mg, 1.45 mmol) racemic-2,2′-bis(diphenylposphino)-1,1′-binapthyl (BINAP) and tris(dibenzylideneacetone)dipalladium (0) (883 mg, 0.964 mmol) and the reaction mixture was heated to 100° C. and reacted at this temperature for 4 hours. The mixture was then cooled to ambient temperature, concentrated under vacuum, treated with DCM, filtered and concentrated under vacuum to give a red solid. The solid was chromatographed on flash silica gel eluting with hexanes/DCM (3:1) to give 7.25 g of C as a red solid.

Workup

  1. customreacted at this temperature for 4 hours
  2. temperatureThe mixture was then cooled to ambient temperature
  3. concentrationconcentrated under vacuum
  4. additiontreated with DCM
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give a red solid
  8. customThe solid was chromatographed on flash silica gel eluting with hexanes/DCM (3:1)
  9. customto give 7.25 g of C as a red solid

Sources & evidence

ORD record
ord-eb1da8f03dc8435a8d46e343d236c3e5
Source dataset
uspto-grants-2006_07
Patent number
US07071337B2

Reaction notes

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