Sodium Carbonate → N-(2-chloro-5-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-6-yl)pyridin-3-yl)dimethylaminosulfonamide

HRID 1963797Notes

Reaction equation

HRID 1963797 reaction equation
[Cl:1][C:2]1(NS(N(C)C)(=O)=O)[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][C:12](=[O:18])[N:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][NH:3]1.ClC1C([NH:39][S:40]([N:43]([CH3:45])[CH3:44])(=[O:42])=[O:41])=CC(B2OC(C)(C)C(C)(C)O2)=CN=1.BrC1C=C2C(N=CC(=O)N2C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[Cl:1][C:2]1[C:7]([NH:39][S:40]([N:43]([CH3:45])[CH3:44])(=[O:42])=[O:41])=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][C:12](=[O:18])[N:11]3[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 582294577-bromo-1-phenylquinoxalin-2(1H)-oneHCID 67088621N-(2-chloro-5-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-6-yl)pyridin-2-yl)dimethylaminosulfonamideHCID 77231275N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)dimethylaminosulfonamide

Product 1

HCID 58229451N-(2-chloro-5-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-6-yl)pyridin-3-yl)dimethylaminosulfonamide

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

N-(2-chloro-5-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-6-yl)pyridin-2-yl)dimethylaminosulfonamide. To a 5 mL microwave tube was added N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)dimethylaminosulfonamide (0.079 g, 0.219 mmol), 7-bromo-1-phenylquinoxalin-2(1H)-one (0.060 g, 0.199 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.015 g, 0.020 mmol), sodium carbonate (0.249 mL, 0.498 mmol), and dioxane (3 mL). The resulting mixture was sealed and subject to microwave heating at 110° C. for 20 min. The reaction mixture was partitioned between pH 7 buffer (1M Tris-HCl) and DCM. The aqueous layer was extracted with DCM (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (12 g, 3% MeOH and 32% EtOAc in DCM) to afford the desired product as a light yellow solid (65.0 mg). MS (ESI pos. ion) m/z: calcd for C21H18ClN5O3S: 455.1; found: 455.8 [M+1]. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.80 (s, 6 H) 6.76-6.86 (m, 2 H) 7.35 (d, J=7.16 Hz, 2 H) 7.53 (d, J=8.33 Hz, 1 H) 7.58-7.72 (m, 3 H) 7.94 (s, 1 H) 8.04 (d, J=8.18 Hz, 1 H) 8.20 (s, 1 H) 8.45 (s, 1 H).

Workup

  1. customThe resulting mixture was sealed
  2. customThe reaction mixture was partitioned between pH 7 buffer (1M Tris-HCl) and DCM
  3. extractionThe aqueous layer was extracted with DCM (2×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (12 g, 3% MeOH and 32% EtOAc in DCM)

Sources & evidence

ORD record
ord-2331e7a57bf84fd0b963dde4e77ce2b3
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

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