Cesium carbonate → HCID 68810823, compound

HRID 1790856Notes

Reaction equation

HRID 1790856 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[N:7]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=4)[N:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.[C:30]([O:34][C:35](=[O:43])[NH:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([CH3:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[Cs+].[Cs+].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>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:30]([O:34][C:35](=[O:43])[NH:36][CH:37]1[CH2:42][CH2:41][N:40]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:12]=2[N:11]=[C:10]([N:7]2[C:6]4[CH:28]=[CH:29][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[N:9]=[CH:8]2)[CH:19]=[CH:18]3)[CH2:39][CH2:38]1)([CH3:33])([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7238334-(N-Boc-amino)piperidineHCID 21037680HCID 21037680, compound

Product 1

HCID 68810823HCID 68810823, compound

Reagents, catalysts & solvents 2

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

Procedure

Trifluoro-methanesulfonic acid 2-(5-methoxy-benzoimidazol-1-yl)-quinolin-8-yl ester F (15.0 9, 35.4 mmol) and piperidin-4-yl-carbamic acid tert-butyl ester (14.2 9, 70.9 mmol) were dissolved in 200 mL of dioxane under an atmosphere of dry N2. To this solution was added Cs2CO3 (16.2 g, 49.6 mmol), racemic-BINAP (1.28 9, 2.12 mMol) and tris(dibenzylideneacetone)dipalladium (0) (1.29 9, 1.41 mMol) and the reaction mixture was heated to 100° C. and reacted at this temperature overnight. The mixture was then cooled to ambient temperature, filtered, and concentrated under vacuum to give an orange foam. The foam was chromatographed on flash silica gel eluting with a gradient from ethyl acetate (EtOAc)/DCM (1:5) to EtOAc/DCM (7:3) give 12.3 g of G as a slightly yellow solid.

Workup

  1. customreacted at this temperature overnight
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customto give an orange foam
  5. customThe foam was chromatographed on flash silica gel eluting with a gradient from ethyl acetate (EtOAc)/DCM (1:5) to EtOAc/DCM (7:3)
  6. customgive 12.3 g of G as a slightly yellow solid

Sources & evidence

ORD record
ord-d49861d3a01e4b57b560f40d8eaa5b6e
Source dataset
uspto-grants-2006_07
Patent number
US07071337B2

Reaction notes

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