Dimethylformamide → HCID 563927, compound

HRID 68546Notes

Reaction equation

HRID 68546 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[C:9]([C:15]#[N:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[C:1]1([N:7]2[C:12](=[O:13])[N:11]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10](=[O:14])[C:9]([C:15]#[N:16])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 563387HCID 563387, compound

Product 1

HCID 563927HCID 563927, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate c (9 g, 0.042 mol) was added to DMF (80 mL) under an ice bath. To the mixture was added NaH (1.3 g, 0.054 mol) in batch under an ice bath. After stirring for 30 min, benzyl bromide (3.1 mL, 0.042 mol) was added dropwise. After the dropwise addition, the reaction was conducted at 50° C. for 4 h. After completion of the reaction, the reaction solution was poured into water (300 mL). A great deal of solid separated out and was filtered by suction. The filtered cake was washed with water and dried to produce Intermediate j (8.1 g) in a yield of 81%.

Workup

  1. additionAfter the dropwise addition
  2. waitthe reaction was conducted at 50° C. for 4 h
  3. customAfter completion of the reaction
  4. customA great deal of solid separated out
  5. filtrationwas filtered by suction
  6. washThe filtered cake was washed with water
  7. customdried

Sources & evidence

ORD record
ord-f0f5808a8e87425f93585dd81c4da0ed
Source dataset
uspto-grants-2014_09
Patent number
US08822465B2

Reaction notes

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