Sodium Methoxide → 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-thiol

HRID 1818170Notes

Reaction equation

HRID 1818170 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][S:19]C(=O)C)[C:13]([CH2:23][O:24][CH2:25][CH3:26])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][SH:19])[C:13]([CH2:23][O:24][CH2:25][CH3:26])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86593762thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester

Product 1

HCID 219840414-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-thiolYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nitrogen was bubbled through a solution of thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester (1.93 g, 4.42 mmol) in methanol (45 mL), and then sodium methoxide (2.5 mL of 25% by weight in methanol, 11.1 mmol) was added dropwise over a period of three minutes. The yellow solution was stirred at ambient temperature for one hour and then concentrated under reduced pressure. The residue was partitioned between dichloromethane (250 mL) and water (125 mL), and hydrochloric acid (˜3 mL of 2 M) was added to adjust the mixture to pH 7. The aqueous layer was separated and extracted with dichloromethane (50 mL); the combined organic fractions were washed with brine (100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 1.73 g of 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-thiol as a tan solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane (250 mL) and water (125 mL), and hydrochloric acid (˜3 mL of 2 M)
  3. additionwas added
  4. customThe aqueous layer was separated
  5. extractionextracted with dichloromethane (50 mL)
  6. washthe combined organic fractions were washed with brine (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4ddc63f5fe24f978c1a602bafd82d6e
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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