Cesium carbonate → HCID 178424207, 화합물

HRID 2383484노트

반응식

HRID 2383484 반응식
Br[C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1.[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(O)C>[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27332672-Methylphenyl boronic acidHCID 178451611HCID 178451611, 화합물

생성물 1

HCID 178424207HCID 178424207, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

To 77 mM solution of tert-butyl 1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (1.3 mL) in toluene and absolute ethanol (2:1) was added o-tolylboronic acid (0.0136 g, 0.1 mmol) followed by 1M solution of cesium carbonate (0.6 mL) and 1,1-bis(Di-tBuppf)PdCl2 (0.005 g). The reaction mixture was shaken at 110° C. for 24 hours. On completion of the reaction, the reaction mixture was extracted with EtOAc (2×2 mL). The organic layers were combined and concentrated under reduced pressure to give the desired crude product, tert-butyl 1-o-tolyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate as an brown solid, which was used in the next step without any further purification.

후처리

  1. customOn completion of the reaction
  2. extractionthe reaction mixture was extracted with EtOAc (2×2 mL)
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ac4ccd7175724cb48140eafab6f67ee8
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263610B2

반응 노트

불러오는 중…