1,4-Dioxane → 2,2,2-trifluoroethyl 5-(2-(1-methyl-1H-pyrazol-3-yl)-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate

HRID 1473307Notes

Reaction equation

HRID 1473307 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])(=[O:14])=[O:13])=[CH:7]2.C[N:22]1[C:26]([C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=2B(O)O)=[CH:25][CH:24]=[N:23]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOC[CH2:49]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:49][N:23]1[CH:24]=[CH:25][C:26]([C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=2[C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([S:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])(=[O:14])=[O:13])=[CH:7]3)=[N:22]1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 71258947(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acidHCID 866873572,2,2-Trifluoroethyl 5-bromonaphthalene-2-sulfonate

Product 1

HCID 866873632,2,2-trifluoroethyl 5-(2-(1-methyl-1H-pyrazol-3-yl)-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A reaction vial was charged with 2,2,2-trifluoroethyl 5-bromonaphthalene-2-sulfonate (0.082 g, 0.222 mmol), (2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid (0.072 g, 0.267 mmol), potassium phosphate tribasic (0.074 mL, 0.889 mmol) and Pd(PPh3)4 (0.026 g, 0.022 mmol). To this solid mixture was added dioxane (1.010 mL) followed by water (0.101 mL). The head space of the vial was swept with nitrogen and the vial was heated in an oil bath to 80° C. After stirring for 2 hours, LC/MS indicated that the reaction was complete. This reaction mixture was transferred to a separatory funnel containing water and the aqueous layer was washed three times with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to an oil. The mixture was concentrated and purified by MPLC using 80 g of silica gel eluting with 0 to 40% EtOAc in hexanes to afford 0.11 g of 2,2,2-trifluoroethyl 5-(2-(1-methyl-1H-pyrazol-3-yl)-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate.

Workup

  1. customA reaction
  2. customThis reaction mixture was transferred to a separatory funnel
  3. washthe aqueous layer was washed three times with EtOAc
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. concentrationThe mixture was concentrated
  8. custompurified by MPLC

Sources & evidence

ORD record
ord-be717701efeb4d888ec20275da2b7034
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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