Toluene → (2R)-1-(3'-Fluoro-4'-propoxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600936Notes

Reaction equation

HRID 1600936 reaction equation
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:32]=[CH:31][C:18]([O:19][CH2:20][C@H:21]([OH:30])[CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:17][CH:16]=1.[F:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:39]=1[O:40][CH2:41][CH2:42][CH3:43]>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(O)C>[F:33][C:34]1[CH:35]=[C:36]([C:15]2[CH:32]=[CH:31][C:18]([O:19][CH2:20][C@H:21]([OH:30])[CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:17][CH:16]=2)[CH:37]=[CH:38][C:39]=1[O:40][CH2:41][CH2:42][CH3:43]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 16217197(3-Fluoro-4-propoxyphenyl)boronic acidHCID 53756856(2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 54111916(2R)-1-(3'-Fluoro-4'-propoxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 61.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 33a) from toluene (5 ml), aqueous sodium carbonate (2 M, 1 ml), (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.25 g, Example 40a), ethanol (1 ml), 3-fluoro-4-propoxybenzeneboronic acid (0.23 g) and tetrakis(triphenylphosphine)palladium(0) (22 mg) with heating at reflux for 4 hours. The residue obtained after work-up was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a white solid (0.19 g)

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 4 hours
  4. customThe residue obtained after work-up
  5. customwas purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-2e7dba52ad6243f3ab27436f339e66d0
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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