Ammonium Chloride → [4-(3,3-Bis-[1,1';4',1'']terphenyl-4-yl-allylsulfanyl)-2-methyl-phenoxy]-acetic Acid

HRID 9343

Reaction equation

HRID 9343 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27](Br)=[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.B(O)(O)[C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:36][CH:37]=1.[F-].[K+].[Cl-].[NH4+]>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.C1COCC1>[C:2]1([C:41]2[CH:40]=[CH:39][C:38]([C:35]3[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=3)=[CH:43][CH:42]=2)[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([C:32]3[CH:33]=[CH:34][C:35]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:36][CH:37]=3)=[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

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 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 10055479[4-(3,3-Bis-[1,1';4',1'']terphenyl-4-yl-allylsulfanyl)-2-methyl-phenoxy]-acetic Acid

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (225 mg, 0.41 mmol, example 1, step A–B, biphenylboronic acid (163 mg, 0.8 mmol), KF (79 mg, 1.35 mmol), Pd2(dba)3 (23 mg, 25 mmol) and Pd(P(t-Bu)3)2 (26 mg, 51 mmol). THF (6 ml) was added to the solid mixture keeping the mixture under nitrogen. The reaction mixture was stirred at 50° C. for 2 h, followed by 10 h at 70° C. A saturated solution of ammonium chloride (5 ml) was added, and the mixture was extracted with dichloromethane (2×20 ml). The organic phases were dried and evaporated. The residue was purified by HPLC to give the title compound in 55 mg (19%) yield.

Workup

  1. customIn an evaporated schlenk flask kept under nitrogen atmosphere
  2. waitfollowed by 10 h at 70° C
  3. extractionthe mixture was extracted with dichloromethane (2×20 ml)
  4. customThe organic phases were dried
  5. customevaporated
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-eb92e10054a6426ebcb60995047ce53d
Source dataset
uspto-grants-2006_08
Patent number
US07091245B2

Linked notes

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