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

HRID 655222ノート

反応式

HRID 655222 の反応式
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]

参加物

5

反応物 2

HCID 145483436-Bromo-7-fluoroquinolineHCID 178476297HCID 178476297、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-03ee9fde51c54e7ebdbf98d4e677d56a
出典データセット
uspto-grants-2011_12
特許番号
US08071581B2

反応ノート

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