4-Methoxybenzylamine → HCID 59631067, compound

HRID 1431772Notes

Reaction equation

HRID 1431772 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].CC(C)([O-])C.[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:60][O:61][C:62]1[CH:69]=[CH:68][C:65]([CH2:66][NH2:67])=[CH:64][CH:63]=1>CCOC(C)=O.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].C1(C)C=CC=CC=1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:67][CH2:66][C:65]3[CH:68]=[CH:69][C:62]([O:61][CH3:60])=[CH:63][CH:64]=3)=[C:3]([CH3:19])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:5]2)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 754524-MethoxybenzylamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 59631067HCID 59631067, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (2.0 g, 7.33 mmol), sodium tert-butoxide (1.41 g, 14.67 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.504 g, 0.550 mmol), XPhos (0.52 g, 1.100 mmol), 4-methoxybenzylamine (0.95 mL, 7.33 mmol), and toluene (15 mL) was stirred at 110° C. under nitrogen for 3 h. Upon completion, the reaction was cooled to 23° C. and concd. The resulting crude residue was taken up in EtOAc, filtered through Celite, and washed with water and brine. The organic phase was dried over magnesium sulfate and concd, affording a crude material that was purified by column chromatography (silica; 0-50% EtOAc in hexanes) to yield 7-fluoro-N-(4-methoxybenzyl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine as an orange oil. Mass Spectrum (ESI) m/e=374.2 (M+1).

Workup

  1. temperatureUpon completion, the reaction was cooled to 23° C.
  2. filtrationfiltered through Celite
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over magnesium sulfate and concd
  5. customaffording a crude material that
  6. customwas purified by column chromatography (silica; 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-dbd9b577f7db40aa8e04196cdbd15746
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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