Ethyl Bromide → 7-Ethoxy-6-fluoro-2-methylquinoline

HRID 338945Notes

Reaction equation

HRID 338945 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH3:22]>CC(C)=O>[CH2:21]([O:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([CH3:13])=[N:8]2)=[CH:3][C:2]=1[F:1])[CH3:22]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 1363380756-Fluoro-2-methylquinolin-7-ol

Product 1

HCID 709832187-Ethoxy-6-fluoro-2-methylquinolineYield 65.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-fluoro-2-methylquinolin-7-ol (500 mg, 1.41 mmol) (Example 119, Step B), potassium carbonate (585 mg, 4.23 mmol) and bromoethane (308 mg, 2.82 mmol) in acetone (10 mL) were stirred at 70° C. in a sealed tube for 20 hours. After dilution with water (50 mL) the reaction was extracted with DCM. The organic phases were concentrated and the residue purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-ethoxy-6-fluoro-2-methylquinoline (190 mg, 65.6% yield) as a solid.

Workup

  1. extractionAfter dilution with water (50 mL) the reaction was extracted with DCM
  2. concentrationThe organic phases were concentrated
  3. customthe residue purified by reverse phase chromatography (SP4, 25M
  4. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-8bed541d5c104de78e648d9f01b8f606
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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