Methyl iodide → HCID 58763656, compound

HRID 1434712Notes

Reaction equation

HRID 1434712 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=2[C:12]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)=[O:13])[CH:5]=[CH:4][N:3]=1.[C:28](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=2[C:12]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:28])[N:19]=[CH:18]3)=[O:13])[CH:5]=[CH:4][N:3]=1.[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:27]=[CH:26][CH:25]=[CH:24][C:11]=2[C:12]([NH:14][C:15]2[CH:23]=[CH:22][C:21]3[C:17](=[CH:18][N:19]([CH3:28])[N:20]=3)[CH:16]=2)=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58763637HCID 58763637, compound

Product 2

HCID 58763651HCID 58763651, compoundYield 19%HCID 58763656HCID 58763656, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.22 g (10 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(1H-indazol-5-yl)-benzamide is mixed in 30 ml of dimethylformamide while being cooled with ice with 3.6 g (11 mmol) of cesium carbonate and 0.68 ml (11 mmol) of methyl iodide, and it is stirred overnight at room temperature. It is then stirred into 250 ml of ice-cold water, stirring is continued for 15 minutes, and it is suctioned off. The filter cake is very quickly dried and chromatographed on silica gel with a gradient of ethyl acetate:hexane=1:1 to 100:0 as an eluant. 1.79 g (41% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(1-methyl-1H-indazol-5-yl)-benzamide with a melting point of 173.8° C. as well as 830 mg (19% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-5-yl)-benzamide with a melting point of 183.8° C. are obtained.

Workup

  1. stirringstirring
  2. waitis continued for 15 minutes
  3. customThe filter cake is very quickly dried
  4. customchromatographed on silica gel with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-64c35b41aa4f43ccaa483def38d330ff
Source dataset
uspto-grants-2009_11
Patent number
US07615565B2

Reaction notes

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