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

HRID 1621839Notes

Reaction equation

HRID 1621839 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.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

7

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 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

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

Sources & evidence

ORD record
ord-4bd939d802894b9eb17433a085516092
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…