Trimethyl borate → (6-Methoxy-2,4-dimethylpyridin-3-yl)boronic acid

HRID 1043892ノート

反応式

HRID 1043892 の反応式
Br[C:2]1[C:3]([CH3:11])=[N:4][C:5]([O:9][CH3:10])=[CH:6][C:7]=1[CH3:8].C([Li])CCC.[B:17](OC)([O:20]C)[O:18]C.[Cl-].[NH4+]>C1COCC1>[CH3:10][O:9][C:5]1[N:4]=[C:3]([CH3:11])[C:2]([B:17]([OH:20])[OH:18])=[C:7]([CH3:8])[CH:6]=1

参加物

6

反応物 4

HCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 112413813-Bromo-6-methoxy-2,4-dimethylpyridineHCID 178418339Butyllithium

生成物 1

HCID 86686327(6-Methoxy-2,4-dimethylpyridin-3-yl)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

3-bromo-6-methoxy-2,4-dimethylpyridine (150 mg) was added to THF (3 mL). The solution was cooled to −78° C., and n-butyllithium (1.63 M solution in n-hexane, 0.468 mL) was added, followed by stirring at the same temperature for 30 minutes. Trimethyl borate (0.108 mL) was added to the reaction mixture, and the mixture was stirred at −78° C. for 10 minutes and at room temperature for 50 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the reaction mixture was concentrated under reduced pressure. THF was distilled off. The resulting residue was filtered. The solid collected by filtration was washed with water and n-heptane to give the title compound (41 mg).

後処理

  1. stirringthe mixture was stirred at −78° C. for 10 minutes and at room temperature for 50 minutes
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. distillationTHF was distilled off
  4. filtrationThe resulting residue was filtered
  5. filtrationThe solid collected by filtration
  6. washwas washed with water and n-heptane

出典と根拠

ORDレコード
ord-05f898e68bc047cdbc2909f207333051
出典データセット
uspto-grants-2013_10
特許番号
US08563565B2

反応ノート

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