Potassium Carbonate → N-(3-chloroquinoxalin-2-yl)-3-fluorobenzenesulfonamide

HRID 331192

반응식

HRID 331192 반응식
[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Cl:12][C:13]1[C:22](Cl)=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[C:22]([NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)(=[O:9])=[O:10])=[N:21][C:20]2[C:15]([N:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 1509243-Fluorobenzenesulfonamide

생성물 1

HCID 57625365N-(3-chloroquinoxalin-2-yl)-3-fluorobenzenesulfonamide수율 84.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
135 °C

실험 절차

3-fluorobenzenesulfonamide (250 mg, 1.4 mmol), 2,3-dichloroquinoxaline (284.1 mg, 1.4 mmol) and dry K2CO3 (198.4 mg, 1.4 mmol) are dissolved in dry DMF (0.8 ml) and heated up to 135° C. in a sealed tube for 2.5 h. When TLC confirms the completion of the reaction, the reaction mixture is cooled down to rt and quenched by addition of water (4 ml) and AcOH (0.03 ml). The residue obtained is triturated and the resulting solid is filtered and washed with water until neutral pH then dried under vacuum to afford 400 mg (83%) of the title compound as an off white solid. 1H NMR (DMSO-d6) δ 12.8-10.9 (br s, 1H), 8.05-7.62 (m, 7H), 7.54 (td, J=2.0, 8.5 Hz, 1H). HPLC (max plot) 94%; Rt 3.79 min. LC/MS: (ES+): 338.1, (ES−): 336.1.

후처리

  1. customthe completion of the reaction
  2. temperaturethe reaction mixture is cooled down to rt
  3. customquenched by addition of water (4 ml) and AcOH (0.03 ml)
  4. customThe residue obtained
  5. customis triturated
  6. filtrationthe resulting solid is filtered
  7. washwashed with water until neutral pH
  8. customthen dried under vacuum

출처 및 근거

ORD 기록
ord-c3076cf4b3dc4172a67b7cbff330ec16
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877757B2

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