Trimethyl-(6-methylpyrazin-2-yl)stannane → tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 57862노트

반응식

HRID 57862 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]([C:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[Sn](C)(C)[C:32]1[CH:37]=[N:36][CH:35]=[C:34]([CH3:38])[N:33]=1>CN(C)C(=O)C>[CH3:38][C:34]1[N:33]=[C:32]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([C:17]5[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:21][CH:22]=5)[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:37]=[N:36][CH:35]=1

참가 물질

4

반응물 2

HCID 86707041Trimethyl-(6-methylpyrazin-2-yl)stannaneHCID 86707057tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate

생성물 1

HCID 86707059tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate수율 72.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
145 °C

실험 절차

A solution of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate (200 mg, 0.486 mmol) and palladium(0)tetrakis(triphenylphosphine) (56 mg, 0.049 mmol) in N,N-dimethylacetamide 5.0 mL was added trimethyl-(6-methylpyrazin-2-yl)stannane (250 mg, 0.971 mmol). The reaction mixture heated at 145° C. for 40 min in microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc) to give the desired product 165 mg 72% yield.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. additionThe crude product was diluted with EtOAc
  4. washthen washed with water
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc)

출처 및 근거

ORD 기록
ord-5992e1de3d8948f1b7c8e2be5b87529d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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