6-Bromo-7-fluoroquinoline → (7-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester

HRID 655222Notes

Reaction equation

HRID 655222 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][CH:6]=[CH:5]2.[C:13]([O-:16])(=[O:15])[CH3:14].[Br-].[C:18]([Zn+2])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([O:15][C:13](=[O:16])[CH2:14][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][CH:6]=[CH:5]2)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 145483436-Bromo-7-fluoroquinolineHCID 178476297HCID 178476297, compound

Product 1

HCID 68534606(7-Fluoro-quinolin-6-yl)-acetic acid tert-butyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6-bromo-7-fluoro-quinoline (1.04 g, 4.6 mmole) in tetrahydrofuran (1 mL) was added a solution of tert-butylzincbromide acetate (20 mL, 10.4 M in tetrahydrofuran) followed by Pd(PPh3)4 (0.58 g, 0.5 mmole). The mixture was heated in a microwave reactor for 35 min at 120° C. The reaction mixture was quenched with a saturated ammonium chloride (60 mL), and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford the title compound (0.75 g, 63%).

Workup

  1. customThe reaction mixture was quenched with a saturated ammonium chloride (60 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-03ee9fde51c54e7ebdbf98d4e677d56a
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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