Water → 6-Bromo-1-(3-methoxypropyl)-3-methyl-1H-indazole

HRID 2263555Notes

Reaction equation

HRID 2263555 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1OS(C)(=O)=O)(=O)[CH3:2].[CH3:16][O:17][CH2:18][CH2:19][CH2:20][NH:21][NH2:22].C([O-])(=O)C.[NH4+].O>CC1C=CC=CC=1C>[Br:10][C:7]1[CH:6]=[C:5]2[C:4]([C:1]([CH3:2])=[N:22][N:21]2[CH2:20][CH2:19][CH2:18][O:17][CH3:16])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 20516966(3-Methoxypropyl)hydrazineHCID 86071609Methanesulfonic acid 2-acetyl-5-bromophenyl ester

Product 1

HCID 231562236-Bromo-1-(3-methoxypropyl)-3-methyl-1H-indazole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 10.90 g methanesulfonic acid 2-acetyl-5-bromo-phenyl ester, 7.75 g of (3-methoxy-propyl)-hydrazine and 7.17 g of ammonium acetate in 100 ml of o-xylene is refluxed for 3 days with continuous separation of the water which is formed during the reaction. The reaction mixture is then cooled to room temperature and concentrated by evaporation. The title compound is obtained as an orange-yellow oil from the residue by means of flash chromatography (SiO2 60 F). Rf=0.38 (1:1 EtOAc-heptane). Rt=4.52 (gradient I).

Workup

  1. customis formed during the reaction
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bec3df15e1b84ed58a9a21f5fb0d4713
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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