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Cesium carbonate → 5-(4-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1616229
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HRID 1616229 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[CH3:16])(=O)=O.[CH3:19][C:20]([CH3:37])([CH3:36])[CH2:21][N:22]1[C:30]2[C:25](=[N:26][C:27](B(O)O)=[CH:28][CH:29]=2)[N:24]([CH3:34])[C:23]1=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CO.Cl[Cu].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:27]2[N:26]=[C:25]3[N:24]([CH3:34])[C:23](=[O:35])[N:22]([CH2:21][C:20]([CH3:19])([CH3:37])[CH3:36])[C:30]3=[CH:29][CH:28]=2)=[C:8]([CH3:16])[CH:9]=1)(=[O:15])[CH3:14]
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참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 213024274-Acetyl-2-methylphenyl trifluoromethanesulfonateHCID 86691828[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]boronic acid

생성물 1

HCID 866918435-(4-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

시약·촉매·용매 4

HCID 62652
Cuprous chloride
촉매
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매
HCID 887Methanol용매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a microwave vial, 4-acetyl-2-methylphenyl trifluoromethanesulfonate (34-1) (40 mg, 0.14 mmol), [1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]boronic acid (14-1) (56 mg, 0.22 mmol), cesium carbonate (92 mg, 0.28 mmol), CuCl (14 mg, 0.14 mmol), and Bis(diphenylphosphino)ferrocene dicholoropalladium (8 mg, 0.015 mmol) was added under nitrogen and dissolved in DMF (0.7 ml). The suspension was heated overnight at 100° C. The reaction was cooled to room temperature, diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 5-(4-acetyl-2-methylphenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (34-2). MS (M+H)+: observed=352.3, calculated=352.4.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. custompassed through a syringe
  3. filtrationfilter
  4. customThe solution was purified
  5. customthe desired fractions were collected
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bf2b679205c44509b6513e4d1e20764b
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765784B2

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