Water → HCID 21894750, compound

HRID 2216251Notes

Reaction equation

HRID 2216251 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2.Br[CH2:14][CH:15]([CH3:17])[CH3:16].O>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:8]=[CH:7]2.[Br:3][C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:9]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 7619295-bromo-1H-indazole

Product 2

HCID 21894750HCID 21894750, compoundHCID 21941240HCID 21941240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (80% suspension in oil, 0.7 g, 0.023 mol) was suspended in N,N-dimethylformamide (DMF) (10 ml) and then a solution of 5-bromoindazole (4.1 g, 0.021 mol) in DMF (40 ml) was added dropwise over 30 minutes. Once the addition was complete the mixture was stirred at ambient temperature for 75 minutes and then a solution of 1-bromo-2-methylpropane (3.7 g, 0.027 mol) in DMF (25 ml) was added over 10 minutes. The mixture was stirred for 5 hours and was then allowed to stand at ambient temperature overnight. The mixture was poured into water, extracted with diethyl ether and then the organic extract was washed further with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1:1 diethyl ether:hexane to give 5-bromo-1-(2-methylpropyl)indazole (2.67 g) and 5-bromo-2-(2-methylpropyl)indazole (1.49 g), each as an orange oil.

Workup

  1. additionOnce the addition
  2. stirringThe mixture was stirred for 5 hours
  3. waitto stand at ambient temperature overnight
  4. extractionextracted with diethyl ether
  5. extractionthe organic extract
  6. washwas washed further with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel eluting with 1:1 diethyl ether

Sources & evidence

ORD record
ord-db33414f16bc43888bc696ba78736b75
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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