Potassium Carbonate → HCID 58683810, compound

HRID 2047502Notes

Reaction equation

HRID 2047502 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].S([CH2:22][N+:23]#[C-:24])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:24]=[N:23][CH:22]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 986623-Bromo-4-methoxybenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 58683810HCID 58683810, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixed solution of 3-bromo-4-methoxybenzaldehyde (200 mg, 0.93 mmol) in methanol (4 mL) was added tosylmethyl isocyanide (200 mg, 1.02 mmol) and K2CO3 (260 mg, 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-(3-bromo-4-methoxyphenyl)oxazole (o) (190 mg, 80%). Following the procedures analogous to the Suzuki and amide coupling reactions described for Compound 20, Compound 25 was prepared.

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-ba409c376ebe4d01a464c3fa2b53effe
Source dataset
uspto-grants-2013_11
Patent number
US08592486B2

Reaction notes

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