Potassium Carbonate → HCID 90047034, compound

HRID 1505001Notes

Reaction equation

HRID 1505001 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][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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 136628985HCID 136628985, compound

Product 1

HCID 90047034HCID 90047034, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-102664ac801148558fcf538f69ec9fb1
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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