Cesium carbonate → HCID 69558529, compound

HRID 1745919Notes

Reaction equation

HRID 1745919 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[C:16]3[CH:17]=[CH:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH:8]=[CH:7]2.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.C([O-])([O-])=O.[Cs+].[Cs+].[C:83]([O:87][C:88](=[O:96])[NH:89][CH:90]1[CH2:95][CH2:94][NH:93][CH2:92][CH2:91]1)([CH3:86])([CH3:85])[CH3:84]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:83]([O:87][C:88](=[O:96])[NH:89][CH:90]1[CH2:95][CH2:94][N:93]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[C:9]([N:12]2[C:16]4[CH:17]=[CH:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[CH:20][C:15]=4[N:14]=[CH:13]2)[CH:8]=[CH:7]3)[CH2:92][CH2:91]1)([CH3:86])([CH3:84])[CH3:85]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7238334-(N-Boc-amino)piperidineHCID 22226962HCID 22226962, compound

Product 1

HCID 69558529HCID 69558529, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

8-Chloro-2-[5-(3-morpholinopropoxy)-1H-benzimidazol-1-yl]-quinoline 138D (226 mg, 0.53 mMol), racemic-BINAP (50 mg, 0.08 mMol), Cs2CO3 (243 mg, 0.75 mMol), piperidin-4-yl-carbamic acid tert-butyl ester (214 mg, 1.07 mMol), xylenes (1 mL), and Pd(OAc)2 (12 mg, 0.053 mMol) were combined under argon and heated at reflux for 2 days. After allowing the mixture to cool, hexanes were added and decanted off, several times, to remove hexane solubles. The residue was stirred with EtOAc and filtered, and the solids washed with additional EtOAc. The combined EtOAc solutions were evaporated, and the residue chromatographed on silica gel with EtOAc/MeOH elution. Fractions containing the title product 138E were combined and concentrated to provide 130 mg.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 days
  3. temperatureto cool
  4. customdecanted off
  5. customseveral times, to remove hexane solubles
  6. filtrationfiltered
  7. washthe solids washed with additional EtOAc
  8. customThe combined EtOAc solutions were evaporated
  9. customthe residue chromatographed on silica gel with EtOAc/MeOH elution
  10. additionFractions containing the title product 138E
  11. concentrationconcentrated
  12. customto provide 130 mg

Sources & evidence

ORD record
ord-89e200ed365c4e9ea09e46590c83fb26
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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