Cesium carbonate → HCID 58166520, compound

HRID 2167658Notes

Reaction equation

HRID 2167658 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[CH3:21])=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([I:41])[CH:36]=1>CN(C)C=O.C(OCC)(=O)C.O>[I:41][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=1)[CH2:34][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]2=[N:3][C:2]=3[NH2:1])=[C:15]([CH3:21])[CH:16]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27593613-Iodobenzyl bromideHCID 581665094-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol

Product 1

HCID 58166520HCID 58166520, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol (B-4), 1.0 equiv. in dimethylformamide (0.10 M) at 22° C. was added cesium carbonate (1.5 equiv.) and the resulting mixture was allowed to stir for 30 minutes. At this point, 1-(bromomethyl)-3-iodobenzene (1.5 equiv.) was added to this mixture. The reaction mixture was allowed to stir at 55° C. for 18 hours, after which it was diluted with ethyl acetate and water. The biphasic layers were separated and the organic layer was washed twice with water. The organic layer was dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-50% ethyl acetate in hexanes gradient to provide 2-(4-(3-iodobenzyloxy)-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (4-1) as a solid.

Workup

  1. stirringto stir at 55° C. for 18 hours
  2. customThe biphasic layers were separated
  3. washthe organic layer was washed twice with water
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customthe volatiles were removed in vacuo
  6. customThe resulting residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-31cd16c8d2b0419bb1349fd1277406ed
Source dataset
uspto-grants-2015_06
Patent number
US09045470B2

Reaction notes

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