1H-Indazole → HCID 24825964, compound

HRID 1514359Notes

Reaction equation

HRID 1514359 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22](F)[N:21]=2)=[CH:15][CH:14]=1>CN(C)C=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:3]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[N:4]3)[N:21]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 24758Sodium hydrideHCID 58026188HCID 58026188, compound

Product 1

HCID 24825964HCID 24825964, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (325 mg, 8.12 mmol) was added to a solution of indazole (800 mg, 6.77 mmol) in N,N-dimethylformamide (10 mL) and stirred for 30 minutes. (4-Chloro-phenyl)-(6-fluoro-pyridin-2-yl)-amine (1.55 g, 6.77 mmol) was added and the reaction mixture was stirred at 80° C. overnight. The mixture was poured into a stirred ice-water solution and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtrated and concentrated in vacuo. The crude product was purified by column chromatography with ethyl acetate-heptane as eluent to give (4-chloro-phenyl)-(6-indazol-1-yl-pyridin-2-yl)-amine (230 mg, 11%) as an yellow solid. LC-ESI-HRMS of [M+H]+ shows 321.0901 Da. Calc. 321.090699 Da, dev. −1.9 ppm

Workup

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography with ethyl acetate-heptane as eluent

Sources & evidence

ORD record
ord-de7d947e397c42ef97db7b33cb9f67b9
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

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