Propargyl bromide → HCID 20610736, compound

HRID 1839106Notes

Reaction equation

HRID 1839106 reaction equation
[N:1]1([C@H:14]([CH2:17][CH3:18])[CH2:15][OH:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].[CH2:21](Br)[C:22]#[CH:23]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[CH2:23]([O:16][CH2:15][C@H:14]([N:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1)[CH2:17][CH3:18])[C:22]#[CH:21]

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 69666208HCID 69666208, compound

Product 1

HCID 20610736HCID 20610736, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(2R)-2-(1H-Imidazo[4,5-c]quinolin-1-yl)butan-1-ol (19 g, 78.8 mmol) was added to a mixture of sodium hydroxide (124 mL of 50%), dichloromethane (150 mL), benzyltrimethyl ammonium chloride (0.73 g), and propargyl bromide (11.4 mL, 102 mmol). The reaction mixture was allowed to stir at ambient temperature overnight. The reaction mixture was diluted with dichloromethane and water. The aqueous fraction was extracted multiple times with dichloromethane. The organic fractions were combined, washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate to provide 20.9 g of 1-{(1R)-1-[(prop-2-ynyloxy)methyl]propyl}-1H-imidazo[4,5-c]quinoline as a brown liquid.

Workup

  1. extractionThe aqueous fraction was extracted multiple times with dichloromethane
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-72d2326a613943ddab27d2cf83026c2a
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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