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Water → tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387550
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HRID 387550 반응식
[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:7]=1)#[CH:2].I[C:18]1[C:26]2[C:21](=[N:22][CH:23]=[C:24]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:25]=2[N:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)[N:20]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[N:19]=1.O.C(OCC)(=O)C>C1COCC1.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>[CH3:54][O:53][C:50]1[CH:51]=[CH:52][C:47]([CH2:46][N:20]2[C:21]3=[N:22][CH:23]=[C:24]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:25]([N:27]4[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:29][CH2:28]4)=[C:26]3[C:18]([C:2]#[C:1][C:3]3[CH:4]=[N:5][N:6]([CH2:8][C:9]4[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=4)[CH:7]=3)=[N:19]2)=[CH:48][CH:49]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 574219374-Ethynyl-1-(4-methoxybenzyl)-1H-pyrazoleHCID 68760648tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

생성물 1

HCID 68768812tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate
수율 118%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

4-Ethynyl-1-(4-methoxybenzyl)-1H-pyrazole (0.068 g, 0.32 mmol) was added to a solution of tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.10 g, 0.16 mmol), Cu(I)I (0.0015 g, 0.008 mmol), PdCl2(PPh3)2 (0.0056 g, 0.008 mmol) and TEA (0.11 ml, 0.80 mmol) in THF (10 mL) and stirred at 40° C. for 18 hours. Water (10 mL) and ethyl acetate (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by flash chromatography (hexane:ethyl acetate=5:1) to give tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.134 g, 95%) as a solid. LCMS (APCI+) m/z 710 (M+H)+.

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customwas purified by flash chromatography (hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-378c44584fa34ee49682e880f9736b78
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372842B2

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