Cesium carbonate → HCID 59427305, compound

HRID 1042902Notes

Reaction equation

HRID 1042902 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:32]=[CH:33][C:34]([CH3:38])=[C:35]([OH:37])[CH:36]=5)=[N:23][N:22]=4)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:46][CH2:47][O:48][CH3:49]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:32]=[CH:33][C:34]([CH3:38])=[C:35]([O:37][CH2:46][CH2:47][O:48][CH3:49])[CH:36]=5)=[N:23][N:22]=4)=[CH:18][CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 67317602HCID 67317602, compound

Product 1

HCID 59427305HCID 59427305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-(4-(7-Methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)-2-methylphenol (120 mg, 239 μmol) and cesium carbonate (234 mg, 718 μmol) were combined in DMF and stirred for 5 min. 1-Bromo-2-methoxyethane (66.5 mg, 479 μmol) was added and the mixture was stirred for 1 h. The mixture was then filtered and purified using reverse phase chromatography to provide the titled product. MS: M+H+=560.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. filtrationThe mixture was then filtered
  3. custompurified

Sources & evidence

ORD record
ord-df275f72e3424867832d30c6c9c06b57
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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