Ethyl orthoformate → 1-(7-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 244827Notes

Reaction equation

HRID 244827 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([Br:18])[CH:6]=2.[CH2:19](OC(OCC)OCC)C>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Br:18][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][C:14]([CH3:15])([OH:16])[CH3:17])[CH:19]=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

Product 1

HCID 690804421-(7-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-olYield 95%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

A 2-L round bottom flask was charged with 1-[(3-amino-7-bromoquinolin-4-yl)amino]-2-methylpropan-2-ol (25.5 g, 82.2 mmol), toluene (1 L), pyridine-HCl (0.1 g, 0.82 mmol, 0.01 eq) and triethylorthoformate (13.4 g, 90.4 mmol, 1.1 eq), and the reaction was heated at reflux for 2 hours. The reaction mixture was concentrated to dryness. The resulting pale yellow solid was slurried in 1% aqueous sodium carbonate solution (250 mL), collected by vacuum filtration, and air-dried on the funnel overnight to provide 25 g of 1-(7-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. filtrationcollected by vacuum filtration
  5. customair-dried on the funnel overnight

Sources & evidence

ORD record
ord-6c8890b9ff944ad5bc0633537d4ea459
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

Loading…