Sodium Carbonate → N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 1025396Notes

Reaction equation

HRID 1025396 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1.[Cl:11][C:12]1[C:17]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:12]1[C:17]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:16][C:15]([C:2]2[N:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27638713-Bromoimidazo[1,2-a]pyrimidineHCID 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 46913619N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamideYield 58%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 50 mL round-bottomed flask was added 3-bromoimidazo[1,2-a]pyrimidine (58 mg, 291 μmol, Syntech, Houston, Tex.), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (120 mg, 291 μmol), tetrakis(triphenylphosphine) palladium (34 mg, 29 μmol), aqueous sodium carbonate (2 M, 0.29 mL, 582 μmol), dioxane (3 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 (5 mL) and extracted with CH2Cl2 (5×20 mL). The organic extract was washed with saturated NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2 to give N-(2-chloro-5-(imidazo[1,2-a]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (68 mg, 58% yield). MS (ESI positive ion) m/z: calcd for C17H11ClFN5O2S: 403.0; found: 403.9 (M+1). 1H NMR (300 MHz, MeOH) δ ppm 7.23 (dd, J=6.94, 4.17 Hz, 1H) 7.25-7.36 (m, 2H) 7.84-7.94 (m, 2H) 8.04 (s, 1H) 8.28 (d, J=2.34 Hz, 1H) 8.52 (d, J=2.19 Hz, 1H) 8.70 (dd, J=4.17, 1.83 Hz, 1H) 8.94 (dd, J=6.94, 1.83 Hz, 1H)

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with CH2Cl2 (5×20 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (5 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 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-321801b2f7b64ffa919c809e11c85503
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

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