Sodium Carbonate → 2-[2-Fluoro-4-(furan-3-ylmethyl)-phenyl]propionic acid

HRID 1506872노트

반응식

HRID 1506872 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[C:5]([F:15])[CH:4]=1.[O:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1C(=O)[N-]C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd+]>[F:15][C:5]1[CH:4]=[C:3]([CH2:2][C:18]2[CH:19]=[CH:20][O:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 49837497Methyl 2-[4-(bromomethyl)-2-fluorophenyl]-propionate

생성물 1

HCID 601555332-[2-Fluoro-4-(furan-3-ylmethyl)-phenyl]propionic acid수율 57.9%

시약·촉매·용매 2

HCID 11434313trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II)촉매HCID 8028Tetrahydrofuran용매

실험 절차

Compound 20 (0.88 g, 3.2 mmol) and 3-furanboronic acid (0.54 g, 4.8 mmol) were dissolved in tetrahydrofuran (12 mL) and a 2 M-aqueous solution (4.0 mL) of sodium carbonate. To this solution, trans-bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) [trans-PdBr(N-Succ)(PPh3)2] (25.9 mg, 1.0 mol %) was added and treated in the same manner as in Example 11. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution followed by conventional hydrolysis with potassium hydroxide to give 0.46 g (55%) of compound (22a) of interest as white solid.

후처리

  1. additiontreated in the same manner as in Example 11
  2. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution
  3. customfollowed by conventional hydrolysis with potassium hydroxide

출처 및 근거

ORD 기록
ord-0fd44c0358f444f1952c8d96788858f3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221786B2

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