2-(Di-tert-butylphosphino)biphenyl → HCID 86659390, compound

HRID 1187696Notes

Reaction equation

HRID 1187696 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=2)[CH:5]=[C:4]([Cl:16])[N:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([NH2:26])[CH3:25])=[CH:20][CH:19]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:16][C:4]1[N:3]=[C:2]([NH:26][C@H:24]([C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[CH3:25])[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=2)[CH:5]=1

Participants

8

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 23676156Sodium t-butoxideHCID 86659391HCID 86659391, compound

Product 1

HCID 86659390HCID 86659390, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

145 mg of 2,6-dichloro-4-(1-isopropyl-1H-pyrazol-4-yl)pyridine obtained by Step 2, 87 mg of (S)-(−)-1-(4-fluorophenyl)ethylamine, 34 mg of 2-(di-t-butylphosphino)biphenyl, 109 mg of sodium t-butoxide and 13 mg of palladium acetate were added in turn to 6 ml of degassed toluene, and then the mixture was stirred at 85° C. for 2 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 59 mg of the objective compound as pale yellow powder.

Workup

  1. washThe solution was washed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-072294cfb5a041e7b9b93b82936b9a98
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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