Sodium Carbonate → Tert-butyl 4-[6-[6-(1-ethylpyrazol-4-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate

HRID 57871

反応式

HRID 57871 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18]4)[CH:14]=[N:13][CH:12]=3)[C:4]=2[CH:3]=1.[CH2:31]([N:33]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[N:34]1)[CH3:32].C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH2:31]([N:33]1[CH:37]=[C:36]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([N:17]5[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18]5)[CH:14]=[N:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:35]=[N:34]1)[CH3:32]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 86707066Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate

生成物 1

HCID 86707067Tert-butyl 4-[6-[6-(1-ethylpyrazol-4-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate収率 102.7%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
150 °C

実験手順

A mixture of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate (0.2526 mmol; 108.6 mg), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (0.3789 mmol; 84.16 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.02526 mmol; 21.1 mg), potassium acetate (0.3789 mmol; 0.38 mL) and sodium carbonate (0.3789 mmol; 0.38 mL) in Acetonitrile (10 mL) in a pressure tube was heated under microwave at 150° C. for 15 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were concentrated. The residue was purified on silica eluted with 0 to 5% MeOH in DCM with 1% NH4OH to afford tert-butyl 4-[6-[6-(1-ethylpyrazol-4-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate (127 mg, ˜100%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. concentrationThe combined organic layers were concentrated
  5. customThe residue was purified on silica
  6. washeluted with 0 to 5% MeOH in DCM with 1% NH4OH

出典と根拠

ORDレコード
ord-cfa5379407e3408fa8d3e1534644b6ac
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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