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

HRID 655222노트

반응식

HRID 655222 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
120 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-03ee9fde51c54e7ebdbf98d4e677d56a
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071581B2

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