Benzophenone imine → N-(Diphenylmethylene)-5-fluoroquinolin-7-amine

HRID 1812247Notes

Reaction equation

HRID 1812247 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([F:12])[CH:3]=1.[C:13](=[NH:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.[NH4+].[Cl-].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]>[C:20]1([C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:26][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[N:9]3)=[C:4]([F:12])[CH:3]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 666003857-Bromo-5-fluoroquinoline

Product 1

HCID 86647070N-(Diphenylmethylene)-5-fluoroquinolin-7-amine

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-bromo-5-fluoroquinoline (128 mg, 0.566 mmol), benzophenone imine (0.143 mL, 0.849 mmol, Aldrich), Pd(dba)2 (32.6 mg, 0.057 mmol, Strem), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (70.5 mg, 0.113 mmol, Aldrich) and sodium 2-methylpropan-2-olate (82 mg, 0.849 mmol, Aldrich) in toluene (4 mL) was stirred at 110° C. for 5 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with saturated NH4Cl (10 mL) and extracted with EtOAc (2×40 mL). The combined organic extracts were washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow solid, which was used for the next step without purification.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe combined organic extracts were washed with saturated NaCl (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90a76b356b6b4eebb1ca47e48abc5093
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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