Sodium Carbonate → N-(2-chloro-5-(4-(2-methoxy-3-pyridinyl)-6-quinolinyl)-3-pyridinyl)-4-fluorobenzenesulfonamide

HRID 1963780Notes

Reaction equation

HRID 1963780 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[CH:24][CH:23]=[C:22]3Cl)=[CH:4][N:3]=1.O.[CH3:31][O:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[CH:35][N:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O1CCOCC1>[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([C:19]2[CH:28]=[C:27]3[C:26](=[CH:21][CH:20]=2)[N:25]=[CH:24][CH:23]=[C:22]3[C:38]2[C:33]([O:32][CH3:31])=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 441197962-Methoxypyridine-3-boronic acid hydrateHCID 44608916N-(2-chloro-5-(4-chloroquinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Product 1

HCID 44609701N-(2-chloro-5-(4-(2-methoxy-3-pyridinyl)-6-quinolinyl)-3-pyridinyl)-4-fluorobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

(Some starting materials may be obtained from Frontier Scientific, Inc., Logan, Utah) To a 5 mL CEM microwave tube was added N-(2-chloro-5-(4-chloroquinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.07 g, 0.2 mmol), 2-methoxypyridine-3-boronic acid hydrate (0.07 g, 0.5 mmol), sodium carbonate (0.2 mL, 0.5 mmol), Pd fibrecat PPh (20% wt, 15 mg), and dioxane (3 mL). The vial was sealed and placed into CEM microwave for 20 min. at 120° C., with 100 watts of power. LC/MS showed a desired product mass as a major peak. The reaction mixture was partitioned between DCM/water. The aqueous layer was extracted with DCM (2×10 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 (12 g) chromatography with hexanes:acetone=80%:20% as the solvent system to afford the desired product as light yellow solid (25 mg). MS (ESI pos. ion) m/z: calc'd for C26H18ClFN4O3S: 520.1; found: 521.3 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.95 (s, 3 H) 7.06-7.19 (m, 3 H) 7.42 (d, J=4.53 Hz, 1 H) 7.67 (dd, J=7.31, 1.90 Hz, 1 H) 7.72 (d, J=1.90 Hz, 1 H) 7.75-7.82 (m, 2 H) 7.90 (dd, J=8.77, 2.05 Hz, 1 H) 8.20 (d, J=2.34 Hz, 1 H) 8.31 (d, J=8.77 Hz, 1 H) 8.34 (d, J=2.19 Hz, 1 H) 8.40 (dd, J=5.04, 1.97 Hz, 1 H) 9.03 (d, J=4.38 Hz, 1 H).

Workup

  1. customThe vial was sealed

Sources & evidence

ORD record
ord-c5a815e986464339b5405f4aeb44322c
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

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