Sodium Carbonate → N-(2-chloro-5-(cinnolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 1963781Notes

Reaction equation

HRID 1963781 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[CH:5]2.[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(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[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[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[N:7][CH:6]=[CH:5]3)=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 112295606-bromocinnolineHCID 218864351,4-Dioxane--water (1/1)HCID 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 44609702N-(2-chloro-5-(cinnolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamideYield 5.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

(Some starting materials may be obtained from Inogent Laboratories Private Lmited, Begumpet Hyerabad, India) A glass microwave reaction vessel was charged with 6-bromocinnoline (150 mg, 0.7 mmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (296 mg, 0.7 mmol), anhydrous sodium carbonate (228 mg, 2.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (37 mg, 0.05 mmol) and dioxane-H2O (2:1, 3 mL). The reaction vessel was sealed and the mixture was stirred and heated at 100° C. for 1 h. Water was added in, and the suspension was filtered, the solid was air-dried. The crude was purified through a Redi-Sep® (Teledyne ISCO, Lincoln, Nebr.) pre-packed silica gel column (40 g), eluting with a gradient of 2% to 5% MeOH in CH2Cl2 to provide N-(2-chloro-5-(cinnolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (15 mg, 5.0% yield) as a yellow solid. MS (ESI pos. ion) m/z: calc'd for C19H12ClFN4O2S:414.8.0; found: 415.0 (MH+). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.44(t, J=8.78 Hz, 2 H) 7.83 (dd, J=8.78, 5.27 Hz, 2 H) 8.24 (s, 1 H) 8.28-8.31 (m, 2 H) 8.46 (s, 1 H) 8.60 (d, J=9.03 Hz, 1 H) 8.79 (s, 1 H) 9.46 (d, J=5.52 Hz, 1 H) 10.60 (s, 1 H).

Workup

  1. customA glass microwave reaction vessel
  2. customThe reaction vessel was sealed
  3. filtrationwas filtered
  4. customthe solid was air-dried
  5. customThe crude was purified through a Redi-Sep® (Teledyne ISCO, Lincoln, Nebr.) pre-packed silica gel column (40 g)
  6. washeluting with a gradient of 2% to 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-4b08d13e291d4a079058ac76b8bc752f
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

Loading…