Toluene → 4-{4-[3-(4-Fluorophenyl)ureido]phenoxy}furo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 853492Notes

Reaction equation

HRID 853492 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1.[CH3:18][O:19][C:20]([C:22]1[O:38][C:25]2=[N:26][CH:27]=[CH:28][C:29]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=3)=[C:24]2[CH:23]=1)=[O:21]>C(#N)C>[CH3:18][O:19][C:20]([C:22]1[O:38][C:25]2=[N:26][CH:27]=[CH:28][C:29]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:16]([NH:15][C:12]4[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=4)=[O:17])=[CH:33][CH:32]=3)=[C:24]2[CH:23]=1)=[O:21]

Participants

5

Reactant 3

HCID 1140TolueneHCID 709554-Fluorophenyl isocyanateHCID 589314624-(4-Aminophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester

Product 1

HCID 589313564-{4-[3-(4-Fluorophenyl)ureido]phenoxy}furo[2,3-b]pyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding toluene (1 ml), acetonitrile (0.5 ml) and 4-fluorophenyl isocyanate (0.02 ml) to 4-(4-aminophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester (28 mg), the mixture was heated to reflux for 30 minutes. After cooling, the precipitated crystals were filtered off and washed with toluene to obtain the title compound (24 mg) as light yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were filtered off
  5. washwashed with toluene

Sources & evidence

ORD record
ord-df22510595574a3a8eae266abaebee88
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

Loading…