Dimethylformamide → Irsenontrine

HRID 1043971노트

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HRID 1043971 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([C@H:16]4[CH2:20][CH2:19][O:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[CH3:21][O:22][C:23]1[C:28]([CH3:29])=[C:27](B(O)O)[C:26]([CH3:33])=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:21][O:22][C:23]1[C:28]([CH3:29])=[C:27]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:15]([C@H:16]5[CH2:20][CH2:19][O:18][CH2:17]5)[N:14]=[CH:13][C:7]=4[C:8](=[O:12])[NH:9][C:10]=3[CH:11]=2)[C:26]([CH3:33])=[CH:25][N:24]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 86686333HCID 86686333, 화합물HCID 136387814(S)-7-bromo-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one

생성물 1

HCID 136253996Irsenontrine

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회

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온도
100 °C

실험 절차

(S)-7-bromo-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one (100 mg), (2-methoxy-3,5-dimethyl-pyridin-4-yl)boronic acid (65 mg) obtained in Preparation Example 29 (4) and cesium carbonate (293 mg) were added to a mixed solution of DMF (5 mL) and water (1 mL) at room temperature. PdCl2(PPh3)2 (10.5 mg) was added to the mixture in a nitrogen gas stream. The mixture was stirred at 80° C. for one hour and at 100° C. for 4.5 hours. After cooling the reaction mixture to room temperature, water (5 mL) was added, and the mixture was extracted with isopropyl acetate. The organic layer was washed with water and brine and then concentrated under reduced pressure. A crude purified product (64.7 mg) was obtained as the title compound. The instrumental data of this compound were identical to those of the (−)-form of Example 25.

후처리

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionthe mixture was extracted with isopropyl acetate
  3. washThe organic layer was washed with water and brine
  4. concentrationconcentrated under reduced pressure
  5. customA crude purified product (64.7 mg)

출처 및 근거

ORD 기록
ord-261d236098c04660b56b4640e6b2f56c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563565B2

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