Potassium Carbonate → HCID 90047034、化合物

HRID 1505001ノート

反応式

HRID 1505001 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 136628985HCID 136628985、化合物

生成物 1

HCID 90047034HCID 90047034、化合物収率 94.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-102664ac801148558fcf538f69ec9fb1
出典データセット
uspto-grants-2015_12
特許番号
US09216965B2

反応ノート

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