Sodium hydride → HCID 18007587, compound

HRID 844252Notes

Reaction equation

HRID 844252 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4]I.[Cl:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[CH:17]=2)[CH:12]=[N:11]1.[S:24]1[CH:28]=[CH:27][C:26]([C:29]2[CH:37]=[C:36]3[C:32]([CH:33]=[N:34][NH:35]3)=[CH:31][CH:30]=2)=[CH:25]1.[H-].[Na+]>CN(C=O)C>[Cl:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[CH:17]=2)[CH:12]=[N:11]1.[Cl:1][CH2:2][CH2:3][CH2:4][N:34]1[CH:33]=[C:32]2[C:36]([CH:37]=[C:29]([C:26]3[CH:27]=[CH:28][S:24][CH:25]=3)[CH:30]=[CH:31]2)=[N:35]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 180074976-(Thiophen-3-yl)-1H-indazoleHCID 22612932HCID 22612932, compound

Product 2

HCID 18007527HCID 18007527, compoundYield 28%HCID 18007587HCID 18007587, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-chloropropyl)-6-(3-thienyl)-1H-indazole 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%).

Workup

  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)

Sources & evidence

ORD record
ord-29b9d96453f743dd99baafe3c54c9106
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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