Potassium Carbonate → HCID 68430980, compound

HRID 2088491Notes

Reaction equation

HRID 2088491 reaction equation
[Br:1][C:2]1[S:6][C:5](C=O)=[CH:4][C:3]=1[CH3:9].S([CH2:20][N+:21]#[C-:22])(C1C=CC(C)=CC=1)(=O)=O.[C:23]([O-:26])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1([C:23]2[O:26][CH:22]=[N:21][CH:20]=2)[S:6][CH2:5][CH:4]=[C:3]1[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 164141925-Bromo-4-methylthiophene-2-carbaldehyde

Product 1

HCID 68430980HCID 68430980, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixed solution of 5-bromo-4-methyl-thiophene-2-carbaldehyde (k) (0.93 mmol) in methanol (4 mL) was added tosylmethyl isocyanide (1.02 mmol) and K2CO3 (1.88 mmol). The reaction was stirred at room temperature for 5 min before heated to 80° C. in the sealed tube. After 30 min, the solution was cooled to room temperature and concentrated. Column chromatography afforded 5-bromo-4-methyl-5-(oxazol-5-yl)-thiophene (l) (190 mg, 80%). Compound (n) was prepared using a Suzuki Coupling reaction analogous to step B of the preparation of Example 1. 1-(2,6-difluoro-phenyl)-3-[4-(5-oxazol-5-yl-3-methyl-thiophen-2-yl)-phenyl]-urea was prepared by reacting (n) with 2,6-difluorophenyl isocyanate by an analogous procedure as that described for Example 4.

Workup

  1. temperaturebefore heated to 80° C. in the sealed tube
  2. waitAfter 30 min
  3. temperaturethe solution was cooled to room temperature
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-931449952935413cab8c5c8efab69322
Source dataset
uspto-grants-2013_05
Patent number
US08435996B2

Reaction notes

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