Ethyl 3,4-Diaminobenzoate → 4-Methoxycarbonylphenylboronic acid

HRID 330760

反応式

HRID 330760 の反応式
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8](N)=[C:7](N)[CH:6]=1)C.[B:14]1(B2OC(C)(C)C(C)(C)O2)[O:18]C(C)(C)C(C)(C)[O:15]1.C([O-])(=O)C.[K+]>O1CCOCC1.C(OCC)(=O)C.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>[CH3:1][O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([B:14]([OH:18])[OH:15])=[CH:7][CH:6]=1)=[O:13]

参加物

7

反応物 3

HCID 458855Ethyl 3,4-DiaminobenzoateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diborane

生成物 1

HCID 27343694-Methoxycarbonylphenylboronic acid収率 228.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

Referring to Scheme 11-1, to a solution of the bromide 1 (2.0 g, 4.2 mmol, prepared according to published conditions) in dioxane (60 mL) was added bis(pinacolato)diboron (4.32 g, 17 mmol), Pd(PPh3)4 (0.49 g, 0.42 mmol) and potassium acetate (2.06 g, 21 mmol) under nitrogen atmosphere. The reaction mixture was stirred at 80° C. for 5 h, and then diluted with ethyl acetate (150 mL). The organic phase was washed with H2O (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was further purified by silica gel column chromatography (haxanes/ethyl acetate=1/4 to 0/1 (v/v)) to give 2 (1.73 g, 79% yield). LC-MS (ESI): m/z 523.3 (M+H)+.

後処理

  1. washThe organic phase was washed with H2O (20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was further purified by silica gel column chromatography (haxanes/ethyl acetate=1/4 to 0/1 (v/v))

出典と根拠

ORDレコード
ord-a76ba1f3b0ac456bb8cdf65b35c10a73
出典データセット
uspto-grants-2014_11
特許番号
US08877707B2

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