Dichloromethane → HCID 178497395, compound

HRID 591687Notes

Reaction equation

HRID 591687 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH2:14][OH:15])=[O:4].ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:36]1[CH:41]=[CH:40][CH2:39][CH2:38][CH2:37]1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH2:14][O:15][CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][O:36]1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 178497394HCID 178497394, compound

Product 1

HCID 178497395HCID 178497395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxymethyl-1H-indazole-5-carboxylic acid methyl ester (0.32 g, 1.55 mmol) in a mixture of anhydrous dichloromethane and THF (2:1, 60 mL) was added pyridinium p-toluene sulfonate (0.08 g, 0.31 mmol) and then 3,4-dihydro-2H-pyran (0.19 g, 2.32 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours under nitrogen. Solvent was evaporated; water (100 mL) was added, and the mixture was extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave 3-(tetrahydro-pyran-2-yloxymethyl)-1H-indazole-5-carboxylic acid methyl ester as a yellow gummy material. Yield: 0.55 g (crude). This product was used in next step without further purification.

Workup

  1. customSolvent was evaporated
  2. additionwater (100 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (100 mL)
  4. washThe organic phase was washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-6ab43dea0fd24525832e77e59ea33173
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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