Potassium Carbonate → HCID 90047039, compound

HRID 1505002Notes

Reaction equation

HRID 1505002 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 90047039HCID 90047039, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-cc733bbf5f4844eab948245d3ebc0899
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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