Sodium hydride → HCID 25115872, compound

HRID 408659Notes

Reaction equation

HRID 408659 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:23])[CH:8]=2)[N:3]=1.[H-].[Na+].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>CN(C=O)C.O>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][O:23][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 68725752HCID 68725752, compound

Product 1

HCID 25115872HCID 25115872, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Methyl-4-(3-phenylpyrrolidin-1-yl)quinolin-6-ol (0.05 g; see Example 42 below) was stirred with sodium hydride (60% dispersion in mineral oil; 0.035 g) in DMF (2 mL) for 15 minutes, after which 4-methoxybenzyl bromide (0.12 g) was added. After 18 hours, the reaction mixture was diluted with water and extracted with dichloromethane, washed with water, dried (MgSO4), filtered and evaporated to give a brown oil. The residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and methanol. Evaporation of the desired fractions gave the title compound as a cream solid.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil
  7. customThe residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and methanol
  8. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-41f4343460ba4b4c90505dab7f24434e
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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