Cesium carbonate → 1-(4-Fluorophenyl)-6-chloro-5-methoxy-1H-indazole

HRID 13120

Reaction equation

HRID 13120 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:4]3[C:5](=[CH:8][C:9]([O:10][CH3:11])=[C:2]([Cl:1])[CH:3]=3)[CH:6]=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 69982(4-Fluorophenyl)hydrazineHCID 149282684-Chloro-2-fluoro-5-methoxybenzaldehyde

Product 1

HCID 593398871-(4-Fluorophenyl)-6-chloro-5-methoxy-1H-indazole

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-fluoro-5-methoxy benzaldehyde (204 mg, 1.1 mmol) and 4-fluorophenylhydrazine (176 mg, 1.1 mmol) were dissolved in N-methylpyrrolidine (5 mL). After addition of cesium carbonate (1.15 g, 3.3 mmol) the mixture was heated in a microwave reactor (CEM Discovery, 150 Watt) to 150° C. for 20 min. After dilution with DCM the mixture was washed with sat. NaHCO3, brine and the organic phase was evaporated. After purification of the crude by flash chromatography on silica gel 253 mg (84%) of the subtitle compound were obtained.

Workup

  1. washAfter dilution with DCM the mixture was washed with sat. NaHCO3, brine
  2. customthe organic phase was evaporated
  3. customAfter purification of the crude by flash chromatography on silica gel 253 mg (84%) of the subtitle compound
  4. customwere obtained

Sources & evidence

ORD record
ord-c1adadd15d2a4e29a6a6d4c16ded8b2c
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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