Methyl iodide → HCID 58138786, compound

HRID 2382953Notes

Reaction equation

HRID 2382953 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:17]=3[CH:18]=[CH:19][CH:20]=2)=[O:11])[CH:5]=[CH:4][NH:3]1.[C:28]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[CH3:28][N:3]1[CH:4]=[CH:5][C:6]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:17]=3[CH:18]=[CH:19][CH:20]=2)=[O:11])=[CH:7][C:2]1=[O:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 44469657HCID 44469657, compound

Product 1

HCID 58138786HCID 58138786, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-amide (50 mg, 0.1 mmol) in DMF (1.0 mL) was added K2CO3 (45.8 mg, 0.331 mmol) followed by iodomethane (0.017 mL, 0.28 mmol). The mixture was warmed at 60° C. for 3 hours. The mixture was diluted with water (10 mL), and a white solid was obtained by filtration. The solid was washed with water (5×10 mL) and air dried. The resulting solid was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in CH2Cl2 to afford the title compound as a white solid.

Workup

  1. customa white solid was obtained by filtration
  2. washThe solid was washed with water (5×10 mL) and air
  3. customdried
  4. customThe resulting solid was purified by silica gel chromatography
  5. washeluting with a gradient of 0-5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-a7cabe6812e04be9a32da744cae2bbc4
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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