Water → HCID 178480236, compound

HRID 845663Notes

Reaction equation

HRID 845663 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CO[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][C:22]([Br:26])=[CH:23][CH:24]=3)[NH:19][N:18]=2)[CH2:13][CH2:12]1)=O.O>C1COCC1>[Br:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([CH:14]3[CH2:15][CH2:16][N:11]([CH3:9])[CH2:12][CH2:13]3)=[N:18][NH:19]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178501914HCID 178501914, compound

Product 1

HCID 178480236HCID 178480236, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of LiAlH4 (6.2 g, 0.083 mol of a 50-55% oil dispersion) in THF (175 ml), under nitrogen, was added, dropwise, 4-(6-bromo-1H-indazol-3-yl)piperidine-1-carboxylic acid methyl ester (28.1 g, 0.083 mol) of Example 106 (a). The reaction was refluxed for 1 hour, cooled in an ice bath, and water was added. The reaction was filtered and the filtrate was concentrated to yield 13.5 g of a solid. The solid was recrystallized from toluene to yield 10.2 g (42%) of a solid, mp 203°-205° C. An analytical sample was obtained by chromatography of a 3.4 g sample on a preparative HPLC (silica gel column) utilizing CH2Cl2 --CH3OH--(C2H5)2NH (95:4:1) as eluent. After evaporation of the appropriate fractions there remained 2.8 g of 6-bromo-3-(1-methyl-4-piperidinyl)-1H-indazole, mp 205°-207° C.

Workup

  1. additionunder nitrogen, was added
  2. temperatureThe reaction was refluxed for 1 hour
  3. temperaturecooled in an ice bath
  4. filtrationThe reaction was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b9ef1a015a9148baa5e578160cfb1d9f
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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