Trimethyl borate → (4-(1H-imidazol-1-yl)-2-methoxyphenyl)boronic acid

HRID 1027174ノート

反応式

HRID 1027174 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[O:13][CH3:14].C([Li])CCC.[B:20](OC)([O:23]C)[O:21]C>C1COCC1>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:20]([OH:23])[OH:21])=[C:3]([O:13][CH3:14])[CH:4]=2)[CH:12]=[CH:11][N:10]=[CH:9]1

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 847077921-(4-bromo-3-methoxyphenyl)-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 86710567(4-(1H-imidazol-1-yl)-2-methoxyphenyl)boronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 1-(4-bromo-3-methoxyphenyl)-1H-imidazole in THF (5 mL) was added 2.5 M n-butyl lithium in hexanes (0.348 ml, 0.869 mmol) dropwise at −78° C. over 15 min. After addition was complete, the reaction solution was stirred at −78° C. for 15 min, and trimethyl borate (0.353 mL, 3.16 mmol) was added. The reaction was allowed to warm to RT, and continued to stir overnight. The reaction was quenched with 1 M HCl aqueous solution to pH 2, diluted with water and extracted with DCM (3×). The product remained in the aqueous solution which was concentrated in vacuo to give crude (4-(1H-imidazol-1-yl)-2-methoxyphenyl)boronic acid (120 mg, MS: 219.2 [M+H+]).

後処理

  1. additionAfter addition
  2. temperatureto warm to RT
  3. stirringto stir overnight
  4. customThe reaction was quenched with 1 M HCl aqueous solution to pH 2
  5. additiondiluted with water
  6. extractionextracted with DCM (3×)
  7. concentrationwas concentrated in vacuo

出典と根拠

ORDレコード
ord-72ddd791864547208faa52aa37c0a43f
出典データセット
uspto-grants-2014_05
特許番号
US08729263B2

反応ノート

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