Potassium Carbonate → N-(2-Chloro-5-(3-chloroquinoxalin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 1963793Notes

Reaction equation

HRID 1963793 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([Cl:12])=[N:9]2)=[CH:4][CH:3]=1.[Cl:13][C:14]1[C:19]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(P(C(C)(C)C)C1C=CC=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC=CC=1)(C)C.Cl[Pd]Cl.O1CCOCC1>[Cl:13][C:14]1[C:19]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:18][C:17]([C:2]2[CH:11]=[C:10]3[C:5](=[CH:4][CH:3]=2)[N:6]=[CH:7][C:8]([Cl:12])=[N:9]3)=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 49132537-Bromo-2-chloroquinoxalineHCID 53363355n-[2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-4-fluorobenzene-1-sulfonamide

Product 1

HCID 53363527N-(2-Chloro-5-(3-chloroquinoxalin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamideYield 40.5%

Reagents, catalysts & solvents 2

HCID 56649816Dichlorobis((di-tert-butyl)phenylphosphine)palladium(II)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a 5 mL microwave vial, 7-bromo-2-chloroquinoxaline (0.100 g, 0.410 mmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.189 g, 0.457 mmol), dichlorobis(di-tert-butylphenylphosphine)palladium(II) (0.0138 g, 0.0222 mmol) and potassium carbonate (0.513 ml, 1.03 mmol) were mixed into 1,4-dioxane (4 mL). The mixture was degassed by bubbling nitrogen through for 5 min. The reaction mixture was stirred at 90° C. for 1.5 h. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. Upon addition of DCM, precipitate came out and it was collected via filtration to afford a white solid (0.0746 g) as the desired product. The filtrate was purified by silica gel column chromatography (eluent: EtOAc in hexanes 0%-50%) to afford another 0.0512 g of the product. The combine yield was 0.1258 g. MS (ESI pos. ion) m/z calcd for C19H11C12FN4O2S: 448.0; found 448.8 [M+1]. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.38-7.50 (m, 2 H) 7.79-7.89 (m, 2 H) 8.18-8.35 (m, 3 H) 8.40 (d, J=1.75 Hz, 1 H) 8.80 (d, J=2.34 Hz, 1 H) 9.05 (s, 1 H) 10.56 (br. s., 1 H).

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through for 5 min
  3. customThe reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  5. washThe combined organic phases were washed with saturated aqueous NaCl (40 mL)
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionUpon addition of DCM, precipitate
  10. filtrationit was collected via filtration

Sources & evidence

ORD record
ord-45557ea7cab644309b9260c884b8e4bf
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

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