Hydrogen Bromide → HCID 14032592, compound

HRID 2107387Notes

Reaction equation

HRID 2107387 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.[CH2:19]([Br:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Br>CN(C)C=O.CCOCC.O>[BrH:26].[C:20]1([CH2:19][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]3)=[N:11]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178480237HCID 178480237, compound

Product 1

HCID 14032592HCID 14032592, compoundYield 44.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of 0.86 g of sodium hydride (50% oil dispension) in 50 ml of dimethylformamide under nitrogen, was added, dropwise, 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole dissolved in 15 ml of hot dimethylformamide. After stirring one hr at ambient temperature, 2.6 g of benzyl bromide in 5 ml of dimethylformamide was added. The reaction mixture was stirred at ambient temperature for 15 hrs and then poured into water. The aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with water, brine and dried over anhydrous magnesium sulfate. The ethyl acetate was evaporated in vacuo to yield an oil. The oil was dissolved in ether and gaseous hydrogen bromide was passed through the solution to yield an oily material. The oily material was triturated with boiling ethyl acetate. The solid was collected and recrystallized from absolute ethanol to yield 2.4 g (44.3%) of product, mp 218°-220° C.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at ambient temperature for 15 hrs
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe ethyl acetate was evaporated in vacuo
  8. customto yield an oil
  9. customto yield an oily material
  10. customThe oily material was triturated with boiling ethyl acetate
  11. customThe solid was collected
  12. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-5543261c97264d7dabd89638d633bca3
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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