Cesium carbonate → 2-{[5-amino-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

HRID 1062795ノート

反応式

HRID 1062795 の反応式
[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:13]([CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[N:12]=[C:11]([OH:24])[C:10]=1[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([O:4][CH2:5][CH2:6][O:24][C:11]1[C:10]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)=[C:9]([NH2:8])[N:13]([CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[N:12]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178423918HCID 178423918、化合物

生成物 1

HCID 234003092-{[5-amino-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate収率 46.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Bromoethyl acetate (0.29 g) was added dropwise over 1 minute to a stirred suspension of 5-amino-1-{2-[(tert-butyl)dimethylsilyl]oxyethyl}-4-(4-methylphenyl)-1-H-pyrazol-3-ol (0.60 g) (Preparation 31) and caesium carbonate (1.69 g) in anhydrous dimethylformamide (10 ml), under a nitrogen atmosphere, at room temperature. The resulting mixture was stirred overnight. The reaction was quenched by adding 1.0M citric acid (40 ml) and the resulting aqueous mixture was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with water (40 ml), brine (40 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography using a Biotage Flash™ 40 column at 10 psi, with a step gradient of ethyl acetate/hexane (1:3 to 1:2) to give the title compound as a yellow oil (0.35 g).

後処理

  1. customThe reaction was quenched
  2. additionby adding 1.0M citric acid (40 ml)
  3. extractionthe resulting aqueous mixture was extracted with ethyl acetate (2×50 ml)
  4. washThe combined organic extracts were washed with water (40 ml), brine (40 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-917ce46b87164a24aec0decdb3bc7f12
出典データセット
uspto-grants-2005_11
特許番号
US06962923B2

反応ノート

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