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

HRID 387529노트

반응식

HRID 387529 반응식
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[CH:11]1([C:14]2[C:15]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[C:16]3[C:22]([I:23])=[N:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH:11]1([C:14]2[C:15]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[C:16]3[C:22]([I:23])=[N:21][N:20]([CH2:2][C:3]4[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=4)[C:17]3=[N:18][CH:19]=2)[CH2:12][CH2:13]1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178452207HCID 178452207, 화합물

생성물 1

HCID 68761344tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate수율 57.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

1-(Chloromethyl)-4-methoxybenzene (0.734 g, 4.69 mmol) was slowly added to a stirring mixture of tert-butyl 4-(5-cyclopropyl-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (2.00 g, 4.26 mmol) and potassium carbonate (0.883 g, 6.39 mmol) in DMF (30 mL) at room temperature, and the reaction was then stirred for 2 hours. EtOAc (200 mL) and water (100 mL) were added to the mixture, and the phases were separated. The organic suspension was washed with water (3×50 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the crude as an oil. The residue was purified by flash chromatography on silica gel (Biotage Flash 40M+) eluting with 15% EtOAc/hexane to provide tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (1.44 g, 57% yield) as a solid.

후처리

  1. customthe phases were separated
  2. washThe organic suspension was washed with water (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude as an oil
  7. customThe residue was purified by flash chromatography on silica gel (Biotage Flash 40M+)
  8. washeluting with 15% EtOAc/hexane

출처 및 근거

ORD 기록
ord-e6901438a55e4b84a7b66ec940023126
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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