2-Chloro-N,N-dimethylethylamine → 4-(2-(Dimethylamino)ethoxy)benzeneboronic acid, pinacol ester

HRID 57522

반응식

HRID 57522 반응식
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

생성물 1

HCID 425989244-(2-(Dimethylamino)ethoxy)benzeneboronic acid, pinacol ester수율 67.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (258 mg, 0.509 mmol) in DMF (10 mL) was added 60% NaH (204 mg, 5.09 mmol) and 2-chloro-N,N-dimethylethylamine (220 mg, 1.527 mmol). The resulting solution was stirred at 60° C. overnight, cooled to the ambient temperature, quenched with aqueous NH4Cl, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give the title compound (100 mg, 29% yield).

후처리

  1. temperaturecooled to the ambient temperature
  2. customquenched with aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-5c4cc35536eb44ccb0ccbb0975931d8d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

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