Sodium hydride → HCID 18007587, 화합물

HRID 988109노트

반응식

HRID 988109 반응식
[Cl:1][CH2:2][CH2:3][CH2:4]I.[S:6]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[N:16][NH:17]3)=[CH:13][CH:12]=2)=[CH:7]1.[H-].[Na+]>CN(C=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][N:17]1[C:18]2[C:14](=[CH:13][CH:12]=[C:11]([C:8]3[CH:9]=[CH:10][S:6][CH:7]=3)[CH:19]=2)[CH:15]=[N:16]1.[Cl:1][CH2:2][CH2:3][CH2:4][N:16]1[CH:15]=[C:14]2[C:18]([CH:19]=[C:11]([C:8]3[CH:9]=[CH:10][S:6][CH:7]=3)[CH:12]=[CH:13]2)=[N:17]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 180074976-(Thiophen-3-yl)-1H-indazole

생성물 2

HCID 18007527HCID 18007527, 화합물수율 28%HCID 18007587HCID 18007587, 화합물수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-chloro-3-iodopropane (0.14 mL, 1.3 mmol) was added to a DMF (3 mL) solution of 6-(3-thienyl)-1H-indazole (88.4 mg, 0.44 mmol) and sodium hydride (60%, 72 mg, 1.8 mmol) that had been allowed to stir for 5 min at room temperature under argon. The reaction mixture was allowed to stir at room temperature overnight before quenching with brine (20 mL) and partitioning into ethyl acetate (100 mL), and drying over anhydrous sodium sulfate. The solvent was removed in vacuo and flash chromatography (silica gel, 10-20% ethyl acetate in hexane) yielded 1-(3-chloropropyl)-6-(3-thienyl)-1H-indazole (76.6 mg, 63%) as well as the side product 2-(3-chloropropyl)-6-(3-thienyl)-2H-indazole (33.9 mg, 28%).

후처리

  1. stirringto stir at room temperature overnight
  2. custombefore quenching with brine (20 mL)
  3. custompartitioning into ethyl acetate (100 mL)
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo and flash chromatography (silica gel, 10-20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-f0f73879e36a4377907e9d87b1f03a64
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635639B2

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