p-Toluenesulfonic acid → HCID 77230604, compound

HRID 1520045Notes

Reaction equation

HRID 1520045 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[C:19]2[C:25]#[CH:26])=[O:15].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1>COCCOC>[C:25]([C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([C:14]([O:13][CH3:12])=[O:15])[CH:17]=2)[N:21]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[N:20]=1)#[CH:26]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 178438001HCID 178438001, compound

Product 1

HCID 77230604HCID 77230604, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

PTSA (0.99 g; 5.77 mmol; 0.11 eq.) was added to a solution of 3-Ethynyl-1H-indazole-5-carboxylic acid methyl ester (10.1 g; 50.2 mmol; 1.0 eq.) and 3,4-dihydro-2H-pyran (10.5 mL; 116 mmol; 2.3 eq.) in DME (100 mL). The reaction mixture was refluxed for 3 h, then cooled and concentrated. The residue was redissolved in DCM and washed sequentially with NaHCO3 (sat) and NaCl (sat) solutions, dried over magnesium sulfate, filtered and concentrated. The crude was triturated with Et2O to give the title compound as a yellow solid

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in DCM
  5. washwashed sequentially with NaHCO3 (sat) and NaCl (sat) solutions
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was triturated with Et2O

Sources & evidence

ORD record
ord-3d1beaf83bdd42d8a2626a8b407974f0
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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