Ethyl bromoacetate → HCID 22596413, compound

HRID 514734Notes

Reaction equation

HRID 514734 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)=[O:19])=[CH:15][CH:14]=[C:13]([OH:28])[CH:12]=2)=[O:10])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=2[NH:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)=[O:19])[O:28][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 22596367N-(5-chloro(2-pyridyl)){6-[(4-cyanophenyl)-carbonylamino]3-hydroxyphenyl}carboxamide

Product 1

HCID 22596413HCID 22596413, compoundYield 112.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of compound N-(5-chloro(2-pyridyl)){6-[(4-cyanophenyl)-carbonylamino]-3-hydroxyphenyl}carboxamide (50 mg, 0.13 mmol) and Cs2CO3 (83 mg, 0.25 mmol) in DMF (1 mL) at room temperature was added ethyl bromoacetate (15 μL, 0.13 mmol). The mixture was stirred for 1 hour before diluted with EtOAc (20 mL) and water (10 mL). The organic layer was washed with brine dried and evaporated to give 70 mg of the crude compound, which was used without farther purification. MS found for C24H19ClN4O5 (M+H)+: 479.0.

Workup

  1. washThe organic layer was washed with brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-be5a496639cc4a9f83cd263f5fb1b23d
Source dataset
uspto-grants-2015_08
Patent number
US09108922B2

Reaction notes

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