Potassium Carbonate → HCID 90047034, 화합물

HRID 1505001노트

반응식

HRID 1505001 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][CH2:29][O:30][CH3:31]>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][CH2:29][O:30][CH3:31])[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 5245511-Bromo-3-methoxypropaneHCID 136628985HCID 136628985, 화합물

생성물 1

HCID 90047034HCID 90047034, 화합물수율 94.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-(tert-Butylsulfonyl)-4-chloroquinolin-7-ol (60 mg, 0.196 mmol), K2CO3 (55 mg, 0.392 mmol) and 1-bromo-3-methoxypropane (0.088 ml, 0.785 mmol) in DMF (1 ml) were heated to 70° C. The reaction mixture was 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 10 g, 30-75% EtOAc/Hexane) to yield 6-(tert-butylsulfonyl)-4-chloro-7-(3-methoxypropoxy)quinoline (0.071 g, 0.185 mmol, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 9H) 1.99-2.08 (m, 2H) 3.27 (s, 3H) 3.58 (t, J=6.19 Hz, 2H) 4.32 (t, J=6.19 Hz, 2H) 7.73 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.65 (s, 1H) 8.94 (d, J=4.55 Hz, 1H), MS: m/z: 372.1 [M+H]+.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and brine
  2. extractionThe aqueous layer was extracted with EtOAc twice
  3. dry with materialthe combined EtOAc layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via Biotage (SNAP Cartridge KP Sil 10 g, 30-75% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-102664ac801148558fcf538f69ec9fb1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216965B2

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