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Cesium carbonate → HCID 67520373、化合物

HRID 1926365
ノート
印刷プレビュー

反応式

HRID 1926365 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:17])=[N:12][CH:13]=[C:14](Br)[CH:15]=1.[C:18]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O:20][CH3:21])=[O:19].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][O:20][C:18](=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([C:14]2[CH:13]=[N:12][C:11]([NH2:17])=[C:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH:15]=2)[CH:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 67389127HCID 67389127、化合物

生成物 1

HCID 67520373HCID 67520373、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21886435
1,4-Dioxane--water (1/1)
溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (1.37 g, 4.5 mmol), 3-(carbomethoxy)phenylboronic acid (0.85 g, 4.7 mmol), Pd(PPh3)4 (5 mol %), and Cs2CO3 (3.5 g, 10.8 mmol) in dioxane/H2O (4:1, 30 mL) were heated under nitrogen at 90° C. for 5 h. Solvents were removed in vacuo, water (10 mL) was added to the residue, and the mixture was extracted with EtOAc (3×10 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material thus obtained was purified by column chromatography on silica gel using mixtures of EtOAc/Hexanes to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=7.28 (brs, 2H), 7.41 (t, J=6.9 Hz, 1H), 7.51 (t, J=6.9 Hz, 1H), 7.64 (d, J=7.5 Hz, 1H), 7.77 (d, J=6.3 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 8.01-8.05 (m, 2H), 8.18 (d, J=2.1 Hz, 1H), 8.26 (t, J=1.8 Hz, 1H), 8.47 (d, J=2.1 Hz, 1H).

後処理

  1. customSolvents were removed in vacuo, water (10 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material thus obtained
  8. customwas purified by column chromatography on silica gel using mixtures of EtOAc/Hexanes

出典と根拠

ORDレコード
ord-6232aea414a84c71976901e646854117
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178668B2

反応ノート

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