Potassium Carbonate → HCID 90047039, 화합물

HRID 1505002노트

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HRID 1505002 반응식
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[OH:18])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:19])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][O:29][CH3:30]>CN(C=O)C>[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:27][CH2:28][O:29][CH3:30])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:19])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 136628985HCID 136628985, 화합물

생성물 1

HCID 90047039HCID 90047039, 화합물수율 46.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-(tert-Butylsulfonyl)-4-chloroquinolin-7-ol (0.81 g, 2.70 mmol), K2CO3 (1.143 g, 8.11 mmol), and 1-bromo-2-methoxyethane (0.508 ml, 5.40 mmol) in DMF (8.50 ml) were heated at 70° C. The reaction mixture cooled and partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc twice and the combined EtOAc layers were dried over Na2SO4, filtered, and concentrated. The residue was purified via Biotage (SNAP Cartridge KP Sil 25 g, 10-50% EtOAc/Hexane) to yield 6-(tert-butylsulfonyl)-4-chloro-7-(2-methoxyethoxy)quinoline (0.461 g, 1.262 mmol, 46.7% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.93 (d, J=4.55 Hz, 1H), 8.66 (s, 1H), 7.73-7.79 (m, 2H), 4.40 (dd, J=3.54, 5.31 Hz, 2H), 3.76 (dd, J=3.66, 5.18 Hz, 2H), 3.34 (s, 3H), 1.33 (s, 9H), MS: m/z: 358.1 [M+H]+.

후처리

  1. temperatureThe reaction mixture cooled
  2. custompartitioned between EtOAc and brine
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. dry with materialthe combined EtOAc layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via Biotage (SNAP Cartridge KP Sil 25 g, 10-50% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-cc733bbf5f4844eab948245d3ebc0899
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216965B2

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