2-Ethylphenylboronic Acid (contains varying amounts of Anhydride) → HCID 59248984, compound

HRID 552301Notes

Reaction equation

HRID 552301 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9](=[O:21])[CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]([CH3:20])[CH:13]=2)[S:5][C:6]=1[CH2:7][CH3:8].[CH2:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O)[CH3:23]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:7]([C:6]1[S:5][C:4]([C:9](=[O:21])[CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]([CH3:20])[CH:13]=2)=[CH:3][C:2]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:22][CH3:23])[CH3:8]

Participants

5

Reactant 2

HCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 67165156HCID 67165156, compound

Product 1

HCID 59248984HCID 59248984, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-Bronno-5-ethyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one (45 mg, 123 μmol) and 2-ethylphenylboronic acid (22 mg, 148 μmol) are dissolved in degassed dioxane (0.8 mL) and degassed 2 M aq. Na2CO3 solution. To this solution PdCl2(dppf) (5 mg, 7 μmol) is added under a stream of argon. The mixture is stirred at 80° C. for 8 h. The mixture is cooled to rt and an aliquot is purified by prep. HPLC to give 1-[5-ethyl-4-(2-ethyl-phenyl)-thiophen-2-yl]-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one as a colourless resin; LC-MS: tR=1.10 min, [M+1]+=383.25.

Workup

  1. customdegassed 2 M aq. Na2CO3 solution
  2. temperatureThe mixture is cooled to rt
  3. customan aliquot is purified by prep

Sources & evidence

ORD record
ord-74389270d77d4f0383c56e39a1639fa0
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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