Ethyl Acetate → (1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

HRID 511344ノート

反応式

HRID 511344 の反応式
[B:1]1([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[O:5]C(C)(C)C(C)(C)[O:2]1.[C:15]([Si:19]([O:22][CH2:23][CH2:24]I)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[Si:19]([O:22][CH2:23][CH2:24][N:13]1[CH:12]=[CH:11][C:10]([B:1]([OH:2])[OH:5])=[N:14]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 219315393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 67260822(1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

In a sealed tube, a suspension of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-pyrazole (100.0 mg, 0.5154 mmol), tert-butyl-(2-iodoethoxy)-dimethylsilane (196 mg, 0.685 mmol), and Cs2CO3 (271 mg, 0.832 mmol) in DMF (3 mL) was stirred at 100° C. for 16 h. The sample was suspended between EtOAc and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving the title material as the boronic acid, as a yellow oil (203.4 mg). MS (ES+): m/z 270.18/271.13/272.15 (19/79/15) [MH+]. HPLC: tR=3.33 min (CAD, ZQ3, polar—5 min).

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5f6d142848174ee7a1a194b2ecbdfb94
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

反応ノート

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