Sodium hydride → 4-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole

HRID 1946980Notes

Reaction equation

HRID 1946980 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 223525484-bromo-1H-indazole

Product 1

HCID 597434944-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazoleYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-1H-indazole (8.831 g, 44.82 mmol) in DMF (100 mL) was added NaH (60% suspension in mineral oil, 74.7 mmol, 2.988 g) followed by 4-chloro-2-methylsulfanyl-pyrimidine (4.34 mL, 37.35 mmol). The resulting mixture was allowed to stir at RT for 2 h; the solid precipitate was collected by filtration, washed and dried under reduced pressure to give 10.7 g (89% yield) of 4-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole.

Workup

  1. filtrationthe solid precipitate was collected by filtration
  2. washwashed
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-056c46ffe59f43dab00cd48c12653859
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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