Hydrochloric Acid → HCID 67520515, compound

HRID 1925316Notes

Reaction equation

HRID 1925316 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:17][C:18]3[C:27]4[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=4)[N:21]=[CH:20][CH:19]=3)=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.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+].C1(C(C2C=CC=CC=2)=[NH:93])C=CC=CC=1.Cl>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:17][C:11]1[CH:10]=[C:15]2[C:14]([CH:9]=[CH:8][C:7]([NH2:93])=[CH:16]2)=[CH:13][CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 86608615HCID 86608615, compound

Product 1

HCID 67520515HCID 67520515, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)naphthalen-2-yl trifluoromethanesulfonate (0.825 g, 1.72 mmol) in THF (30 mL), was added Pd(OAc)2 (0.039, 0.17 mmol), followed by BINAP (0.1187 g, 0.19 mmol) and Cs2CO3 (0.784 g, 2.41 mmol). Diphenylmethanimine was added and the mixture was stirred at 65° C. for 16 h. The reaction was cooled to RT, treated with 1N HCl (12 mL) and stirred for 4 h. The mixture was diluted with water and extracted with EtOAc 3×. The aqueous extract was treated with NH4OH until pH=12. This was extracted with EtOAc 3×. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material was taken on directly without purification. MS (ESI, pos. ion) m/z: 347.4 (M+1).

Workup

  1. temperatureThe reaction was cooled to RT
  2. stirringstirred for 4 h
  3. extractionextracted with EtOAc 3×
  4. extractionThe aqueous extract
  5. additionwas treated with NH4OH until pH=12
  6. extractionThis was extracted with EtOAc 3×
  7. washThe combined organic layers were washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customdirectly without purification

Sources & evidence

ORD record
ord-bd62f80c0f3948f1a23a4f2d3537dffa
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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