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Water → 4-chloro-1-(4-fluorobenzyl)-1H-pyrazolo[4,3-c]pyridine

HRID 2097001
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반응식

HRID 2097001 반응식
[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:16][C:15]3[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 468356374-chloro-1H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 581107234-chloro-1-(4-fluorobenzyl)-1H-pyrazolo[4,3-c]pyridine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To 4-chloro-1H-pyrazolo[4,3-c]pyridine (60 mg, 0.40 mmol) in 2 ml DMF was added 4-Fluorobenzylbromide (0.060 ml, 0.48 mmol) then add NaH (20 mg, 0.4 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 38 mg of major isomer A and 15 mg of minor isomer B.

후처리

  1. extractionextract three times with EtOAc
  2. washPool all organics and wash one time with brine
  3. dry with materialthen dry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate to dryness
  6. customThe residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50)
  7. customto provide 38 mg of major isomer A and 15 mg of minor isomer B

출처 및 근거

ORD 기록
ord-4718b4f4e2984d73931017e1e5bbb7f1
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450343B2

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