Dimethylformamide → 2-(Azidomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)quinoxaline

HRID 2044920노트

반응식

HRID 2044920 반응식
Br[CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:23])[N:4]=1.CN(C=O)C.[N-:29]=[N+:30]=[N-:31].[Na+]>>[N:29]([CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:23])[N:4]=1)=[N+:30]=[N-:31]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 577078262-(Bromomethyl)-5-chloro-3-(2-(trifluoromethyl)-phenyl)quinoxaline

생성물 1

HCID 866306362-(Azidomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)quinoxaline

실험 절차

To a stirring solution of 2-(bromomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)-quinoxaline (0.7173 g, 1.786 mmol) in DMF (8.930 mL, 1.786 mmol) was added sodium azide (0.2322 g, 3.572 mmol) at room temperature and the mixture was stirred at room temperature. After 30 min, the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The organic layer was washed with brine (50 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give bluish-brown syrup. The bluish-brown syrup was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 14 min, then 50% isocratic of EtOAc for 5 min as eluent to give 2-(azidomethyl)-5-chloro-3-(2-(trifluoromethyl)phenyl)quinoxaline: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.20 (1 H, dd, J=8.6, 1.2 Hz), 8.10-8.14 (1 H, m), 7.99 (1 H, d, J=7.8 Hz), 7.95 (1 H, dd, J=8.4, 7.6 Hz), 7.79-7.91 (3 H, m), 4.41-4.67 (2 H, m); LC-MS (ESI) major peak of m/z 364.0 [M+H]+. The crude product was carried on crude without pufrification for the next step.

후처리

  1. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  2. washThe organic layer was washed with brine (50 mL×1)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give bluish-brown syrup
  7. customThe bluish-brown syrup was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column
  8. customover 14 min

출처 및 근거

ORD 기록
ord-ed99456da7ec41629f67b6ab761a53e5
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586739B2

반응 노트

불러오는 중…