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

HRID 1010354Notes

Reaction equation

HRID 1010354 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-a5306cb157cf4d74ac221d9548fbb08a
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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