Dimethyl Sulfoxide → HCID 58447739, compound

HRID 592197Notes

Reaction equation

HRID 592197 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:7][C:8]=1OS(C(F)(F)F)(=O)=O.[CH3:21][C:22]1[CH:27]=[C:26]([Sn](CCCC)(CCCC)CCCC)[CH:25]=[CH:24][N:23]=1.CS(C)=O>CN(C=O)C.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]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:7][C:8]=1[C:26]1[CH:25]=[CH:24][N:23]=[C:22]([CH3:21])[CH:27]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 216605742-Methyl-4-(tributylstannyl)pyridineHCID 58447920HCID 58447920, compound

Product 1

HCID 58447739HCID 58447739, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To the mixture of 2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetic acid 182-2 (590 mg, 1.9 mmol) and 2-methyl-4-(tributylstannyl)pyridine (730 mg, 1.9 mmol) in DMF (2.0 mL) was added [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (33 mg, 0.04 mmol). The reaction was stirred at 110° C. for 20 hours. After cooling down to room temperature, the reaction mixture was diluted into DMSO and purified by reverse-phase HPLC to give 2-(3-methoxy-4-(2-methylpyridin-4-yl)phenyl)acetic acid 182-3. MS m/z 258.1 (M+1).

Workup

  1. temperatureAfter cooling down to room temperature
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-a8a8591ff7bd4b9da904d5951ac4f7b0
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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