Sodium Carbonate → Methyl E-4-{2-[2-(4-cyanophenyl)ethyl]-4-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]but-3-enyl}benzoate

HRID 1672621Notes

Reaction equation

HRID 1672621 reaction equation
Br[C:2]1[CH:39]=[CH:38][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[CH:16]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)[CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[F:40][C:41]([F:52])([F:51])[C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][CH:16](/[CH:15]=[CH:14]/[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]2[CH:38]=[CH:39][C:2]([C:45]3[CH:46]=[CH:47][C:42]([C:41]([F:52])([F:51])[F:40])=[CH:43][CH:44]=3)=[CH:3][CH:4]=2)[CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[CH:31][CH:32]=1)#[N:37]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57864403Methyl E-4-{4-[2-(4-bromobenzyloxy)phenyl]-2-[2-(4-cyanophenyl)ethyl]but-3-enyl}benzoate

Product 1

HCID 57864328Methyl E-4-{2-[2-(4-cyanophenyl)ethyl]-4-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]but-3-enyl}benzoateYield 58%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

270 mg (0.47 mmol) of methyl E-4-{4-[2-(4-bromobenzyloxy)phenyl]-2-[2-(4-cyanophenyl)ethyl]but-3-enyl}benzoate from Example 18A are dissolved in 3 ml of 1,2-dimethoxyethane and, under argon, 106 mg (0.56 mmol) of 4-trifluoromethylphenylboronic acid, 3.3 mg of bis(triphenylphosphine)palladium(II) chloride and 0.51 ml of a 2 M solution of sodium carbonate in water are added. The reaction mixture is then stirred under reflux for 12 hours. The mixture is subsequently cooled, filtered through 1 g of Extrelut, washed with dichloromethane and concentrated. The resulting crude product is purified by preparative HPLC. 175 mg (0.27 mmol, 58% yield) of a colorless solid are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureThe mixture is subsequently cooled
  3. filtrationfiltered through 1 g of Extrelut
  4. washwashed with dichloromethane
  5. concentrationconcentrated
  6. customThe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-259ee7259938433fb278ee2ff144c762
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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