Cesium carbonate → 5-iodo-1-pyridin-2-yl-1H-indazole

HRID 13145

Reaction equation

HRID 13145 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=O.[NH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[NH2:12].C(=O)([O-])[O-].[Cs+].[Cs+].CN1C(=O)CCC1>C(OC(=O)C)C.O>[I:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[N:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[N:12]=[CH:4]2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 786452-HydrazinopyridineHCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 593397925-iodo-1-pyridin-2-yl-1H-indazoleYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Fluoro-5-iodobenzaldehyde (527 mg, 2.11 mmol), 2-hydrazinopyridine (237 mg, 2.17 mmol), cesium carbonate (2.06 g, 6.32 mmol) and NMP (10 ml) werer charged in a 10 ml vial which was sealed and stirred (magnetic bar) over night at 100° C. Water and ethylacetate were added and the phases was separated. The organic layer was washed three times with brine and concentrated. Purification on silica with ethylacetate:heptane 5:95 to 10:90 over 15 min, 10 ml/min, followed by evaporation afforded 31 mg (5%) of 5-iodo-1-pyridin-2-yl-1H-indazole.

Workup

  1. customwas sealed
  2. customthe phases was separated
  3. washThe organic layer was washed three times with brine
  4. concentrationconcentrated
  5. customPurification on silica with ethylacetate:heptane 5:95 to 10:90 over 15 min
  6. custom10 ml/min, followed by evaporation

Sources & evidence

ORD record
ord-fda5b65fee80468c819f78e9c0b3cf4c
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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