Water → (2R)-1-(3'-Aminobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600934Notes

Reaction equation

HRID 1600934 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:25]=[CH:24][C:11]([O:12][CH2:13][C@H:14]([OH:23])[CH2:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:10][CH:9]=1.O.[NH2:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1.O>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:27][C:28]1[CH:33]=[C:32]([C:8]2[CH:25]=[CH:24][C:11]([O:12][CH2:13][C@H:14]([OH:23])[CH2:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:10][CH:9]=2)[CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 53756856(2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 54006807(2R)-1-(3'-Aminobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 82.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Aqueous sodium carbonate solution (2 M, 1.55 ml) was added to a solution of (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.50 g), 3-aminobenzeneboronic acid monohydrate (0.26 g) and tetrakis(triphenylphosphine)palladium(0) (0.045 g) in ethanol (1.72 ml) and toluene (6.9 ml). The mixture was stirred at reflux under a nitrogen atmosphere for 3 hours and then, cooled to room temperature. The reaction mixture was poured into water and then extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (19:1) to give the title compound (0.43 g) as an which was recrystallised from isohexane:ethyl acetate to give a white solid.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (19:1)

Sources & evidence

ORD record
ord-a600fa305fcd4355b87616b37b915bd4
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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