HCID 22180092, compound → HCID 9931460, compound

HRID 992393Notes

Reaction equation

HRID 992393 reaction equation
[F:1][C:2]1[C:10]2[O:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([C:11]([O:13]C)=[O:12])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[CH3:23].C[Si](C)(C)[O-].[K+]>O1CCCC1>[F:1][C:2]1[C:10]2[O:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[CH3:23]

Participants

4

Reactant 2

HCID 22180092HCID 22180092, compoundHCID 23668039Potassium trimethylsilanolate2×

Product 1

HCID 9931460HCID 9931460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution comprised of methyl 7-fluoro-6-(4-iodo-2-methyl-phenylamino)-1H-benzooxazole-5-carboxylate (0.024 M) in tetrahydrofuran is added solid potassium trimethylsilanolate (5.14 equiv.). The reaction mixture is stirred at ambient temperature under argon for 16 hours. An additional equivalent of potassium trimethylsilanolate is added and the mixture stirred 30 minutes. The reaction mixture is concentrated in vacuo to give a residue that is then taken up into 1:1 (v/v)ethyl acetate-diethyl ether. The organic phase is washed with dilute aqueous hydrochloric acid, water, and brine, is dried (MgSO4), is concentrated in vacuo, and chased with chloroform to give a crude product. Recrystallization from an appropriate solvent like ethanol gives the purified desired product. cl Example 6

Workup

  1. stirringthe mixture stirred 30 minutes
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customto give a residue that
  4. washThe organic phase is washed with dilute aqueous hydrochloric acid, water, and brine
  5. dry with materialis dried (MgSO4)
  6. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-b5511b7d7adf4b03a582d36e063ee8ba
Source dataset
uspto-grants-2002_10
Patent number
US06469004B1

Reaction notes

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