Methanol → tert-butyl 4-(5-cyclopropyl-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387530노트

반응식

HRID 387530 반응식
[CH:1]1([C:4]2[C:5]([N:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[C:6]3[C:12](I)=[N:11][N:10]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[F-].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH3:52][OH:53]>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[C:5]([N:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[C:6]3[C:12]([O:53][CH3:52])=[N:11][N:10]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 13181,10-PhenanthrolineHCID 522689Potassium FluorideHCID 68761344tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

생성물 1

HCID 68757913tert-butyl 4-(5-cyclopropyl-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate수율 72.1%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
110 °C

실험 절차

tert-Butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.35 g, 0.59 mmol), Cu(I)I (113 mg, 0.59 mmol), KF on Al2O3 (40%) (241 mg, 4.15 mmol), 1,10-phenanthroline (107 mg, 0.59 mmol) and MeOH (1.2026 mL, 29.688 mmol) were placed in toluene (3 mL), degassed under argon, and then heated to 110° C. overnight. The reaction was then cooled to room temperature. EtOAc was added, and the reaction was filtered through celite and washed with EtOAc. The filtrate was then concentrated, and the resulting residue was purified by column chromatography (1:1 hexanes:EtOAc) to give the product tert-butyl 4-(5-cyclopropyl-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.21 g, 71% yield).

후처리

  1. customdegassed under argon
  2. temperatureThe reaction was then cooled to room temperature
  3. additionEtOAc was added
  4. filtrationthe reaction was filtered through celite
  5. washwashed with EtOAc
  6. concentrationThe filtrate was then concentrated
  7. customthe resulting residue was purified by column chromatography (1:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-6de7822b1ce34c479562dcd1037af2ed
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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