Binap, (A+-)- → HCID 57972830, compound

HRID 661453Notes

Reaction equation

HRID 661453 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=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.[CH2:60]([C@@H:62]1[CH2:71][C@H:70]([NH2:72])[C:69]2[C:64](=[CH:65][CH:66]=[C:67]([C:73]([F:76])([F:75])[F:74])[CH:68]=2)[NH:63]1)[CH3:61].CC(C)([O-])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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O>[N:8]1([C:5]2[CH:4]=[CH:3][C:2]([NH:72][C@@H:70]3[C:69]4[C:64](=[CH:65][CH:66]=[C:67]([C:73]([F:76])([F:74])[F:75])[CH:68]=4)[NH:63][C@H:62]([CH2:60][CH3:61])[CH2:71]3)=[N:7][CH:6]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

9

Reactant 4

HCID 634876Binap, (A+-)-HCID 230921314-(6-Bromopyridin-3-yl)morpholineHCID 23676156Sodium t-butoxideHCID 24969672(2R,4S)-2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine

Product 1

HCID 57972830HCID 57972830, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

4-(6-Bromo-pyridin-3-yl)-morpholine (3.16 g), tris(dibenzylideneacetone)-dipalladium (806 mg), and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.2 g) were dissolved in toluene (60 ml) and the mixture was stirred under nitrogen atmosphere at 50° C. for an hour. The reaction mixture was cooled to room temperature, thereto was added the compound obtained in Example 8 (1) dissolved in toluene (10 ml) and the mixture was stirred at room temperature for 15 minutes. The stirring was further continued at 50° C. overnight after addition of sodium tert-butoxide (1.86 g). Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo to give the titled compound. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→3:2) to give the titled compound (1.1 g). MS (m/z): 407 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 15 minutes
  3. customthe organic layer was separated
  4. washwashed with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c0988cd44c5497e93a4ca6f73a841ca
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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