Methanol → HCID 178434256, compound

HRID 598827Notes

Reaction equation

HRID 598827 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.CO.C[O-].[Na+].[CH3:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH:29]=[O:30])[CH:27]=2)[NH:22][N:21]=1>O>[CH3:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]3[O:30][CH:12]=[N:11][CH:10]=3)[CH:27]=2)[NH:22][N:21]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 161915Tosylmethyl isocyanideHCID 10942334Sodium MethoxideHCID 178434286HCID 178434286, compound

Product 1

HCID 178434256HCID 178434256, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 150 mL round-bottom flask was added p-toluenesulfonylmethyl isocyanide (1.46 g, 7.5 mmol) and MeOH, followed by sodium methoxide (4.60 mL, 21.2 mmol) and a MeOH solution of 3-methyl-1H-indazole-5-carbaldehyde (1.00 g, 6.24 mmol) (prepared as described in WO 2007/124288). 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 the vacuum oven overnight to give 3-methyl-5-(oxazol-5-yl)-1H-indazole (1.01 g, 81% yield) as a tan powder. LCMS (API-ES) m/z (%): 200 (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 the vacuum oven overnight

Sources & evidence

ORD record
ord-059dca73ed0b4588a0b4676b74e6add1
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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