Cesium carbonate → HCID 58292666、化合物

HRID 1798161ノート

反応式

HRID 1798161 の反応式
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27628474-Chloro-2-nitropyridineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

生成物 1

HCID 58292666HCID 58292666、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (2 g, 8 mmol, 1 eq.) and 4-chloro-2-nitropyridine (2.53 g, 16 mmol, 2 eq.) in 50 ml of DMF was added cesium carbonate (7.8 g, 24 mmol, 3 eq.). The reaction was stirred at room temperature overnight. It was then quenched by water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (DCM/methanol=19:1 to 4:1) to give desired product as light yellow oil. MS (ESI) m/z=743 [2M−H]+.

後処理

  1. customIt was then quenched by water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography on silica gel (DCM/methanol=19:1 to 4:1)

出典と根拠

ORDレコード
ord-74154f53fcdd4e2caebb28aa66a3f2a4
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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