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

HRID 252370
Notes
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Reaction equation

HRID 252370 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 7237
O-Xylene
Solvent

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 60F). 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-f7b92177327a47ed90865467c01f2ce8
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07868036B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes