Diethyl Ether → tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387581노트

반응식

HRID 387581 반응식
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[I:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:19]=2[N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[NH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C.O>[I:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:19]=2[N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[N:14]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=2)[N:13]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178452208HCID 178452208, 화합물

생성물 1

HCID 68760648tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

1-(Chloromethyl)-4-methoxybenzene (0.128 mL, 0.938 mmol) was added to tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.395 g, 0.782 mmol) and K2CO3 (0.130 g, 0.938 mmol) in DMF (10 mL). The reaction was stirred at room temperature for 2 hours. Ether (30 mL) and water (10 mL) were then added. The organic layer was separated, washed with brine, and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.33 g, 68%) as a solid. 1H NMR (400 Hz, CD2Cl2) δ 8.23 (s, 1H), 7.44 (m, 3H), 7.33 (d, J=8.8 Hz, 2H), 7.26 (m, 2H), 6.84 (d, J=8.8 Hz, 2H), 5.59 (s, 2H), 3.76 (s, 3H), 3.55 (m, 4H), 2.86 (m, 4H), 1.40 (s, 9H).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate, 3:1)

출처 및 근거

ORD 기록
ord-c61e0c95ed044d138f77c70dff932191
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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