Water → HCID 58887669、化合物

HRID 1767206

反応式

HRID 1767206 の反応式
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br:21][C:22]1[CH2:26][CH2:25][CH2:24][C:23]=1Br.O>C1(C)C(CCO)=CC=CC=1>[CH3:11][O:10][C:8](=[O:9])[C:6]1[CH:5]=[C:4]([C:23]2[CH2:24][CH2:25][CH2:26][C:22]=2[Br:21])[CH:3]=[C:2]([NH2:1])[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2737799380430-56-8HCID 44385281,2-Dibromocyclopentene

生成物 1

HCID 58887669HCID 58887669、化合物収率 87%

試薬・触媒・溶媒 1

HCID 882672-Methylphenethyl alcohol溶媒

実験手順

(3-amino-5-methoxycarbonylphenyl)boronic acid (2.66 g, 13.6 mmol), Pd(0) [PPh3]4 (1.57 g, 1.36 mmol), potassium carbonate (15 g, 108 mmol) and 1,2-dibromocyclopentene (12 g, 53 mmol) in toluene-ethanol (1:1 60 mL) were stirred at 90° C., under nitrogen, for 2 hrs. Upon cooling, the reaction mixture was poured into water and extracted with ethyl acetate (40×3 mL). The combined organic layers were dried over MgSO4 and concentrated. Purification was carried out on a Biotage® using isohexane containing a gradient of ethyl acetate (0–20%) to give the required product as yellow solid (3.5 g, 87%). 1H NMR (CDCl3):1.96–2.0 (2H,m), 2.50 (2H,t,J=7.4), 2.67 (2H,t,J=7.4), 3.80 (2H,bs), 3.88 (3H,s), 7.14 (1H,s), 7.28 (1H,s), 7.59 (1H,s). LC/MS[MH+]=296, 298 Rt=3.38.

後処理

  1. temperatureUpon cooling
  2. extractionextracted with ethyl acetate (40×3 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customPurification

出典と根拠

ORDレコード
ord-61e2c6af0c1447afa971e8a974fff372
出典データセット
uspto-grants-2007_06
特許番号
US07232821B2

関連ノート

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