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

HRID 387540노트

반응식

HRID 387540 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 (734 mg, 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, see Example J) and potassium carbonate (883 mg, 6.39 mmol) in DMF (30 mL) at room temperature. After 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. The residue obtained 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. LCMS (APCI+) m/z 590.1 (M+H)+.

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. customThe residue obtained
  7. customwas purified by flash chromatography on silica gel (Biotage Flash 40M+)
  8. washeluting with 15% EtOAc/hexane

출처 및 근거

ORD 기록
ord-808f441f9fd34e49acbe471748c980c1
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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