Cesium carbonate → 3-Fluoro-3'-(trifluoromethyl)-(1,1'-biphenyl)-4-carboxylic acid

HRID 2038441Notes

Reaction equation

HRID 2038441 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[C:14]([O-:17])([O-])=[O:15].[Cs+].[Cs+].O1[CH2:25][CH2:24]OCC1>CCO.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]>[F:1][C:2]1[CH:3]=[C:8]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)[CH:7]=[CH:24][C:25]=1[C:14]([OH:17])=[O:15]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 167687113-Fluoro-3'-(trifluoromethyl)-(1,1'-biphenyl)-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of compound 26a (75 mg, 0.345 mmol), compound 15b (80 mg, 0.42 mmol), and Cs2CO3 (282 mg, 0.864 mmol) in dioxane (9 mL) and EtOH (3 mL) was added Pd(dppf)Cl2 (0.0252 g, 0.0345 mmol). The reaction mixture was stirred at 80° C. for 3 h. After cooling, the solid was removed by filtration and washed with CH3OH. The filtrate was concentrated. The crude compound 26b was purified by reverse phase chromatography.

Workup

  1. temperatureAfter cooling
  2. customthe solid was removed by filtration
  3. washwashed with CH3OH
  4. concentrationThe filtrate was concentrated
  5. customThe crude compound 26b was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-46b6f53d924b44cf8662183df3888ee5
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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