Sodium Carbonate Decahydrate → tert-butyl 4-(6-(6-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 57808

반응식

HRID 57808 반응식
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[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[CH2:30]([N:32]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[N:33]1)[CH3:31].O.C([O-])(=O)C.[K+].O.O.O.O.O.O.O.O.O.O.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>[CH2:30]([N:32]1[CH:36]=[C:35]([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[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:21][CH2:22]5)[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:34]=[N:33]1)[CH3:31]

참가 물질

7

반응물 4

HCID 151402Sodium Carbonate DecahydrateHCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 23702041Potassium acetate hydrateHCID 86707015Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate

생성물 1

HCID 86707016tert-butyl 4-(6-(6-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
150 °C

실험 절차

A mixture of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate (0.5112 mmol; 212.1 mg), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (1.022 mmol; 227.1 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.05112 mmol; 42.6 mg), potassium acetate hydrate (0.7668 mmol; 0.77 mL) and sodium carbonate decahydrate (0.7668 mmol; 0.77 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 layer was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford tert-butyl 4-(6-(6-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate as a dark tan solid.

후처리

  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 layer was concentrated
  5. customThe residue was purified on silica
  6. washeluted with 0 to 6% MeOH in DCM

출처 및 근거

ORD 기록
ord-d02842cc4687411a82311d0e3b54146b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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