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

HRID 13171

Reaction equation

HRID 13171 reaction equation
F[CH2:2][O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1C=O.Cl.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.ClCCl>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:9]3[C:10](=[CH:11][C:4]([O:3][CH3:2])=[CH:5][CH:8]=3)[CH:22]=[N:21]2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 200615072-(Fluoromethoxy)benzaldehyde

Product 1

HCID 593396221-(4-Fluorophenyl)-5-methoxy-1H-indazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-fluoromethoxybenzaldehyde (2.1 mmol, 320 mg), 4-fluorophenylhydrazine hydrochloride (2.1 mmol, 340 mg) and cesium carbonate (3 mmol, 2.0 g) in NMP (6 ml) was heated in a microwave reactor (300 W, 20 min, 150° C.). After cooling to r.t. the reaction mixture was diluted with dichloromethane (20 ml) and washed with 1M HCl, and sat. NaHCO3. The organic layer was dried over Na2SO4, concentrated, and purified by flash chromatography on silica gel (heptane-ethyl acetate).

Workup

  1. temperatureAfter cooling to r.t. the reaction mixture
  2. washwashed with 1M HCl, and sat. NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica gel (heptane-ethyl acetate)

Sources & evidence

ORD record
ord-c8e87cd6e7c044e2b1f536b44b2227db
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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