Methanol → 6-(Oxazol-5-yl)isoquinoline

HRID 598824Notes

Reaction equation

HRID 598824 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.CO.C[O-].[Na+].[CH:19]1[C:28]2[C:23](=[CH:24][C:25]([CH:29]=[O:30])=[CH:26][CH:27]=2)[CH:22]=[CH:21][N:20]=1>O>[O:30]1[C:29]([C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[CH:19]=[N:20][CH:21]=[CH:22]3)=[CH:12][N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 161915Tosylmethyl isocyanideHCID 10942334Sodium MethoxideHCID 15290359Isoquinoline-6-carboxaldehyde

Product 1

HCID 670625036-(Oxazol-5-yl)isoquinolineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 150 mL round-bottomed flask was added p-toluenesulfonylmethyl isocyanide (3.50 g, 18.0 mmol) and MeOH, followed by sodium methoxide (11.0 mL, 50.9 mmol) and a MeOH solution of isoquinoline-6-carbaldehyde (2.35 g, 15.0 mmol). The solution was stirred at reflux for about 1 hour and followed by LCMS. Water was added (50 mL) and the MeOH was removed in vacuo. The suspension was cooled to 0° C., and the resulting precipitate was filtered and dried in a vacuum oven overnight to give 6-(oxazol-5-yl)isoquinoline (2.50 g, 85% yield) as a tan powder. LCMS (API-ES) m/z (%): (100%, M++H).

Workup

  1. temperatureat reflux for about 1 hour
  2. customthe MeOH was removed in vacuo
  3. filtrationthe resulting precipitate was filtered
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-367fb964e9124a24a857c6bacec884f5
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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