Sodium hydride → HCID 89995998, compound

HRID 1480796Notes

Reaction equation

HRID 1480796 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[CH:13]=[N:14][NH:15][CH:16]=1)[CH:8]=[CH:7][CH:6]=2.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH3:23]>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[CH:16]=[N:15][N:14]([CH2:20][CH2:21][O:22][CH3:23])[CH:13]=1)[CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 89996121HCID 89996121, compound

Product 1

HCID 89995998HCID 89995998, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-chloro-5-(1H-pyrazol-4-yl)isoquinoline (Preparation 3, 10 mg, 0.42 mmol) in DMF (3 mL) was added NaH (60%, 28 mg, 0.122 mmol). After stirring at room temperature for 15 minutes, 1-bromo-2-methoxyethane (25.4 mg, 0.183 mmol) was added and the reaction mixture was stirred at 80° C. for 60 minutes. The reaction was diluted with brine and extracted with EtOAc, the organic layers were dried with Na2SO4 and concentrated in vacuo to afford the title compound that was used in the next step without further purification (15 mg).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 60 minutes
  2. extractionextracted with EtOAc
  3. dry with materialthe organic layers were dried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af907b41bb214dfeb1a90d2c575d58b5
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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