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

HRID 1506871ノート

反応式

HRID 1506871 の反応式
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.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O.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:17]2[S:16][CH:20]=[CH:19][CH:18]=2)[CH:8]=[CH:7][C:6]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 49837497Methyl 2-[4-(bromomethyl)-2-fluorophenyl]-propionate

生成物 1

HCID 601555322-[2-Fluoro-4-(thiophene-2-ylmethyl)-phenyl]propionic acid収率 76%

試薬・触媒・溶媒 2

HCID 11434313trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 20 (0.98 g, 3.8 mmol) and 2-thiopheneboronic acid (0.73 g, 5.7 mmol) were dissolved in tetrahydrofuran (12 mL) and a 2 M-aqueous solution (4.8 mL) of sodium carbonate. To this solution, trans-bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) [trans-PdBr(N-Succ) (PPh3)2] (30.8 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 0.75 g (76%) of compound (21b) of interest as white solid.

後処理

  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

出典と根拠

ORDレコード
ord-69b9ddf63d114b47bd4673a69ac9eba4
出典データセット
uspto-grants-2015_12
特許番号
US09221786B2

反応ノート

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