Triphenylphosphine → 7-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

HRID 2383174Notes

Reaction equation

HRID 2383174 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:4]2[C:13]3[CH:12]=[CH:11][C:10]([OH:14])=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:39]1[CH:43]=[CH:42][C:41]([CH2:44]O)=[CH:40]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:39]1[CH:43]=[CH:42][C:41]([CH2:44][O:14][C:10]2[CH:11]=[CH:12][C:13]3[C:4]4[N:3]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:2]([CH3:1])=[N:15][C:5]=4[CH:6]=[N:7][C:8]=3[CH:9]=2)=[CH:40]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 204493-Furanmethanol2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 1363405372-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol2×

Product 1

HCID 670510517-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolineYield 127.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (300 mg, 1.17 mmol), triphenylphosphine (921 mg, 3.51 mmol), and 3-furanmethanol (173 mg, 1.76 mmol) were slurried in 20 mL of anhydrous THF. After 5 minutes diisopropyl azodicarboxylate (710 mg, 3.51 mmol) was added dropwise to the mixture. The resulting homogeneous solution was stirred six days. Analysis of the reaction by HPLC indicated that mostly starting material was present. Additional portions of triphenylphosphine (150 mg), 3-furanmethanol (0.5 mL) were added followed by diisopropyl azodicarboxylate (1 mL). Analysis of the reaction after 1 hour indicated that all of the 2-methyl-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinolin-7-ol was consumed. The reaction was filtered through an acidic ion-exchange resin with methanol followed by 1M ammonia in methanol. The filtrate was concentrated to give 500 mg of 7-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a dark orange oil.

Workup

  1. customAnalysis of the reaction by HPLC
  2. customAnalysis of the reaction after 1 hour
  3. customwas consumed
  4. filtrationThe reaction was filtered through an acidic ion-exchange resin with methanol
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9d6707cb9842473f90f2517e14a70932
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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