HCID 14576205, compound → HCID 14576224, compound

HRID 232156Notes

Reaction equation

HRID 232156 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)[N:13]=1)=O)C>C1COCC1>[Br:27][C:24]1[CH:23]=[CH:22][C:21]([N:14]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=3[C:12]([CH2:10][OH:9])=[N:13]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14576205HCID 14576205, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14576224HCID 14576224, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.52 g) in THF (100 ml) was treated with 1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid ethyl ester (6.98 g) and reacted at ambient temperature for 2 hours. Additional reagent (1.52 g) was added and the reaction was continued for one hour to complete the conversion. Excess reagent was quenched, the mixture was filtered, and the filtrate was evaporated to yield crude title compound (548 g). Crystallization from acetonitrile gave pure title compound (4.32 g, m.p. 126°-127° C.). The filtrate residue contained equal proportions of title compound and the des-bromo derivative.

Workup

  1. customreacted at ambient temperature for 2 hours
  2. customExcess reagent was quenched
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. customto yield crude title compound (548 g)
  6. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-cdac6200d1524d9588a6aa2d1ae7cd63
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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