(3-Acetamidophenyl)boronic acid → (2R)-1-(3'-Acetamidobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600938Notes

Reaction equation

HRID 1600938 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@H:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[C:20]([NH:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:22])[CH3:21]>C(O)C.C(=O)([O-])[O-].[Na+].[Na+].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>[C:20]([NH:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@H:8]([OH:17])[CH2:9][CH2:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:4][CH:3]=2)[CH:27]=[CH:26][CH:25]=1)(=[O:22])[CH3:21]

Participants

7

Reactant 2

HCID 157274(3-Acetamidophenyl)boronic acidHCID 53756856(2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 53947584(2R)-1-(3'-Acetamidobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 89%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Prepared according to the method described in Example 33a) from (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.50 g), 3-acetamidobenzeneboronic acid (0.38 g) and tetrakis(triphenylphosphine)palladium(0) (0.045 g) in ethanol (1.7 ml), aqueous sodium carbonate solution (2 M, 1.55 ml) and toluene (6.9 ml) with heating at reflux for 1 hour. The residue obtained after work-up was purified by column chromatography over silica eluting with dichloromethane:methanol (92:8) to give the title compound (0.52 g) as an oil which crystallised from ethyl acetate and was recrystallised from isohexane/ethyl acetate.

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 1 hour
  4. customThe residue obtained after work-up
  5. customwas purified by column chromatography over silica eluting with dichloromethane:methanol (92:8)

Sources & evidence

ORD record
ord-c51b1010fffd4f6ea8dd059ff19808b7
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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