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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
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HRID 2209011 반응식
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]
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178439029HCID 178439029, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-66678d11df444beb935874d4c5aa8a06
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376441B2

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