3-Fluorophenol → HCID 68765011, 화합물

HRID 387593

반응식

HRID 387593 반응식
I[C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[C:4]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C([O-])([O-])=O.[Cs+].[Cs+].[F:52][C:53]1[CH:54]=[C:55]([OH:59])[CH:56]=[CH:57][CH:58]=1>CN1C(=O)CCC1.O>[F:52][C:53]1[CH:54]=[C:55]([CH:56]=[CH:57][CH:58]=1)[O:59][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[C:4]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 97433-FluorophenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 68758063tert-butyl 4-(5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

생성물 1

HCID 68765011HCID 68765011, 화합물수율 21%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A solution of tert-butyl 4-(5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.100 g, 0.182 mmol, see Example 13), Cu(I)Cl (0.00901 g, 0.0910 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (0.00950 mL, 0.0455 mmol), Cs2CO3 (0.119 g, 0.364 mmol) and 3-fluorophenol (0.165 mL, 1.82 mmol) in NMP (2 mL) was stirred at 106° C. for 20 hours. The reaction was then cooled to room temperature, and H2O (5 mL) was added. The reaction mixture was then extracted with ethyl acetate (15 mL), washed with brine, and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate, 2.5:1) to give tert-butyl 4-(5-(3-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.020 g, 21%) as a solid. MS APCI (+) m/z 534.4 detected.

후처리

  1. extractionThe reaction mixture was then extracted with ethyl acetate (15 mL)
  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, 2.5:1)

출처 및 근거

ORD 기록
ord-4a14fafd26084d28840f43d2c916844a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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