Sodium Carbonate → HCID 44610007, compound

HRID 1963784

Reaction equation

HRID 1963784 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[C:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O.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>[Cl:12][C:13]1[C:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:17][C:16]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][N:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 5962624-Chloro-1,5-naphthyridineHCID 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 44610007HCID 44610007, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

(Some starting materials may be obtained from Aldrich, St. Louis, Mo.) To a 50 mL round-bottomed flask was added 4-chloro-1,5-naphthyridine (40 mg, 243 μmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (100 mg, 243 μmol), tetrakis(triphenylphosphine)palladium (28 mg, 24 μmol), sodium carbonate (243 μl, 486 μmol), dioxane (2 mL). The reaction mixture was stirred at 100° C. for 5 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (3 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (3 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 70% EtOAc/hexanes to give N-(2-chloro-5-(1,5-naphthyridin-4-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (46 mg, 46% yield) as a white solid. MS (ESI pos. ion) m/z calc'd for C19H12ClFN4O2S: 414.0; found 415.0. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.09 (s, 1 H) 7.13-7.23 (m, J=8.33 Hz, 2 H) 7.68 (d, J=4.38 Hz, 1 H) 7.75 (dd, J=8.55, 4.17 Hz, 1 H) 7.97 (dd, J=8.99, 4.90 Hz, 2 H) 8.49-8.56 (m, J=2.85, 2.85 Hz, 2 H) 8.58 (d, J=2.05 Hz, 1 H) 9.01 (dd, J=4.17, 1.68 Hz, 1 H) 9.10 (d, J=4.38 Hz, 1 H)

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with EtOAc (2×30 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (3 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 70% EtOAc/hexanes

Sources & evidence

ORD record
ord-a6ad25e0f1b641ada53766f596d25e93
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Linked notes

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