Water → HCID 14032567, compound

HRID 652168Notes

Reaction equation

HRID 652168 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.Br[CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CN(C)C=O>[CH2:25]([O:24][C:22]([CH2:21][CH2:20][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]2)=[N:11]1)=[O:23])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 68320Ethyl 3-bromopropionateHCID 178480237HCID 178480237, compound

Product 1

HCID 14032567HCID 14032567, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension, under nitrogen, of 1.7 g of a 50% oil dispersion of sodium hydride in 75 ml of dimethylformamide was added, dropwise, 6.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 30 ml of hot dimethylformamide. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for 1 hr and a solution of 6.5 g of ethyl 3-bromopropionate was added dropwise. The reaction mixture was stirred at ambient temperature for 3 hrs and then poured into water. The aqueous mixture was extracted with ethyl acetate and the extracts were washed with water, dried over anhydrous magnesium sulfate and filtered. Evaporation of the filtrate under vacuum gave 6.5 g (70.8%) of product, as an oil.

Workup

  1. additionUpon completion of the addition
  2. stirringThe reaction mixture was stirred at ambient temperature for 3 hrs
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. washthe extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customEvaporation of the filtrate under vacuum

Sources & evidence

ORD record
ord-6e81caf1335e42ad944fcb64d5c49e42
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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