Potassium Fluoride → 3-{4-[1-(2-[1,3]Dioxan-2-yl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester

HRID 1914331Notes

Reaction equation

HRID 1914331 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][NH:6][C:7](=[O:33])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:19][C:20]2[CH:25]=[CH:24][C:23](Br)=[C:22]([CH:27]3[O:32][CH2:31][CH2:30][CH2:29][O:28]3)[CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[F-].[K+].[CH:37]([C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1)([CH3:39])[CH3:38]>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>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][NH:6][C:7](=[O:33])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:43]3[CH:44]=[CH:45][C:40]([CH:37]([CH3:39])[CH3:38])=[CH:41][CH:42]=3)=[C:22]([CH:27]3[O:32][CH2:31][CH2:30][CH2:29][O:28]3)[CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27734804-Isopropylphenylboronic acidHCID 671536513-{4-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 671535813-{4-[1-(2-[1,3]Dioxan-2-yl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl esterYield 94.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-{4-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (560 mg, 1.05 mmol), potassium Fluoride (183 mg, 3.15 mmol), 4-isopropylphenyl boronic acid (344 mg, 2.1 mmol) and tetrakis(triphenylphosphine)palladium (121 mg, 0.105 mmol) are placed in a flask. After the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml) is added. The resulting solution is refluxed overnight, loaded on silica gel, eluted with hexane and ethyl acetate to give the titled compound (570 mg).

Workup

  1. customAfter the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml)
  2. additionis added
  3. temperatureThe resulting solution is refluxed overnight
  4. washeluted with hexane and ethyl acetate

Sources & evidence

ORD record
ord-1d4301a2a149414fbaae98699e2902fe
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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