Triethylamine → 7-Bromo-2-isopropyl-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8260

반응식

HRID 8260 반응식
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:17]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[N:20][N:19]4[CH2:28][CH2:29][CH2:30][C:18]=34)=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>O1CCCC1.O>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:17]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[N:20][N:19]4[CH2:28][CH2:29][CH2:30][C:18]=34)=[CH:12][C:13]([CH:1]([CH3:3])[CH3:2])=[N:14]2)=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219925197-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolineHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 102247947-Bromo-2-isopropyl-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A 2 M solution of isopropyl magnesium chloride in tetrahydrofuran (65 μL, 0.13 mmol) is added to solution of 7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (50.0 mg, 0.13 mmol) in tetrahydrofuran (1 mL) at room, temperature with stirring for 2 h. The mixture is cooled to −78° C. and triethylamine (21.4 μL, 0.154 mmol) and methanesulfonyl chloride (11 μL, 0.14 mmol) added. The mixture is warmed to room temperature and allowed to stand 18 h. The mixture is treated with water, extracted with ethyl acetate, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (dichloromethane to 75% ethyl acetate/dichloromethane) to yield the title compound as a solid, 4.5 mg (9%).

후처리

  1. temperatureThe mixture is warmed to room temperature
  2. waitto stand 18 h
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (dichloromethane to 75% ethyl acetate/dichloromethane)

출처 및 근거

ORD 기록
ord-b587c4a0071e4ce489f217f216631641
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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