1,1'-Biphenyl-4-yl-boronic acid → HCID 66760170, compound

HRID 2234147Notes

Reaction equation

HRID 2234147 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=2)=[CH:9][CH2:10][S:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=2)=[CH:4][CH:3]=1.[C:31]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:43]3[CH:44]=[CH:45][C:40]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:41][CH:42]=3)=[CH:7][CH:6]=2)=[CH:9][CH2:10][S:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 522689Potassium FluorideHCID 10370262{4-[3,3-Bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid

Product 1

HCID 66760170HCID 66760170, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418851HCID 178418851, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (example 1) (225 mg, 0.410 mmol), 4-biphenylboronic acid (163 mg, 0.82 mmol), KF (79 mg, 1.35 mmol), Pd2(dba)3 (23 mg, 0.025 mmol) and Pd(P(t-Bu)3)2 (25 mg, 0.049 mmol) was evacuated for air and kept under nitrogen. THF (6 ml) was added and the reaction mixture was stirred at 70° C. overnight. A saturated aqueous NH4Cl (5 ml) solution was added, and the mixture was extracted with methylene chloride (2×20 ml). The combined organic phases were dried an evaporated. The isolated products were further purified on column chromatography using methylene chloride:THF (40:1) as eluent. The isolated products were further purified on HPLC using acetonitril:water (7:3) increasing to pure acetonotril as eluent. The title product was isolated as an E/Z mixture in 40 mg (16%) yield.

Workup

  1. customwas evacuated for air
  2. additionTHF (6 ml) was added
  3. additionA saturated aqueous NH4Cl (5 ml) solution was added
  4. extractionthe mixture was extracted with methylene chloride (2×20 ml)
  5. customThe combined organic phases were dried an evaporated
  6. customThe isolated products were further purified on column chromatography
  7. customThe isolated products were further purified on HPLC
  8. temperatureincreasing to pure acetonotril as eluent

Sources & evidence

ORD record
ord-635bc1c25b104fe6ad70c45a92ae8053
Source dataset
uspto-grants-2010_05
Patent number
US07709528B2

Reaction notes

Loading…