Potassium Carbonate → HCID 59633327, compound

HRID 2369108Notes

Reaction equation

HRID 2369108 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28]([F:31])([F:30])[F:29])=[N:9]1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>CCOC(C)=O.O>[CH3:27][S:24]([C:20]1[CH:19]=[C:18]([C:15]2[S:14][C:13]([C:12]3[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[C:34]4[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=4)[N:9]=[C:10]([C:28]([F:31])([F:30])[F:29])[CH:11]=3)=[CH:17][CH:16]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343783-Pyridinylboronic acidHCID 68656338HCID 68656338, compound

Product 1

HCID 59633327HCID 59633327, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a 50 mL round bottom flask attached with condenser was added 1-(2-Bromo-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-3-trifluoromethyl-1H-pyrazole (prepared following the described in Example 1c) (110 mg, 210 μmol), 3-pyridylboronic acid (31 mg, 525 μmol), PdCl2dppf (25 mg, 10 mol %), K2CO3 (58 mg, 410 μmol), 1,4-dioxane (8 mL) and H2O (1.5 mL). The reaction solution was allowed to stir at 75° C. for 20 hrs. The reaction solution was diluted with EtOAc (150 mL) and transferred to a separator), funnel and washed with aq NH4Cl (100 mL) and aq NaCl (100 mL). The organic phase was dried over Na2SO4, filtered, concentrated on the Rotavapor and chromatographed through a 25 g SiO2 column using a mobile phase gradient of 100% Hx to 90% EtOAc to afford 45 mg (41% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (m, 1H), 7.99 (m, 2H), 7.51-7.90 (m, 8H), 7.24 (s, 1H), 7.17-7.23 (m, 2H), 6.87 (d, 1H), 3.28 (s, 3H); 19F NMR (400 MHz, DMSO-d6) δ −61.2 ppm. MS (ES) 526.5 [M+H]+.

Workup

  1. customTo a 50 mL round bottom flask attached with condenser
  2. customprepared
  3. washwashed with aq NH4Cl (100 mL) and aq NaCl (100 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated on the Rotavapor
  7. customchromatographed through a 25 g SiO2 column

Sources & evidence

ORD record
ord-a255ed7d3563406aa3645dac527086e7
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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