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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
ノート
印刷プレビュー

反応式

HRID 1616229 の反応式
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]
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

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 62652
Cuprous chloride
触媒
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒
HCID 887Methanol溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf2b679205c44509b6513e4d1e20764b
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765784B2

反応ノート

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