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Cesium carbonate → 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

HRID 2209011
ノート
印刷プレビュー

反応式

HRID 2209011 の反応式
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[C:5]2[N:10]([CH3:13])[CH:11]=[N:12][C:4]=2[CH:3]=1.ClC1N=C(SC)C2N=CN(C)C=2C=1.[C:27]([N:31]1[CH:35]=[C:34](C2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1)([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-3](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C.O.COCCOC>[C:27]([N:31]1[CH:35]=[C:34]([C:2]2[N:7]=[C:6]([S:8][CH3:9])[C:5]3[N:10]([CH3:13])[CH:11]=[N:12][C:4]=3[CH:3]=2)[CH:33]=[N:32]1)([CH3:30])([CH3:29])[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 1178431521-tert-butyl-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1H-pyrazoleHCID 1178433356-chloro-1-methyl-4-(methylthio)-1H-imidazo[4,5-c]pyridineHCID 1178434146-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

生成物 1

HCID 1178438386-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

試薬・触媒・溶媒

3
HCID 178439029HCID 178439029、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.02 and 6-chloro-1-methyl-4-(methylthio)-1H-imidazo[4,5-c]pyridine 2.03 (prepared as previously described, ˜1:2 mixture of regioisomers, 1.25 g, 5.85 mmol),1-tert-butyl-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1H-pyrazole (2.20 g, 8.78 mmol), and Cs2CO3 (5.72 g, 17.6 mmol) was added DME (20 mL) and water (10 mL) and the solution was degassed for 10 min. [1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (397 mg, 0.585 mmol) was added and the reaction was heated to 100 deg C. for 1 hour. Upon cooling, the aqueous layer was removed, EtOAc and water were added, and the layers separated. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient) to afford 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.39 and 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.40, which were isolated as a mixture and carried directly into the next step.

後処理

  1. customprepared
  2. additionwas added
  3. temperaturethe reaction was heated to 100 deg C
  4. temperatureUpon cooling
  5. customthe aqueous layer was removed
  6. additionEtOAc and water were added
  7. customthe layers separated
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient)

出典と根拠

ORDレコード
ord-66678d11df444beb935874d4c5aa8a06
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376441B2

反応ノート

読み込み中…

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