p-Toluenesulfonic acid → HCID 86673211, compound

HRID 1047526Notes

Reaction equation

HRID 1047526 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[CH:24]=[O:25])([O-:14])=[O:13].[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1>C1COCC1.C(Cl)Cl>[N+:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1)[N:19]=[C:18]2[CH:24]=[O:25])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 178520037HCID 178520037, compound

Product 1

HCID 86673211HCID 86673211, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

p-Toluenesulfonic acid (30 mg, 0.158 mmol) was added to a solution of 5-nitro-indazole-3-carbaldehyde (300 mg, 1.569 mmol) and 3,4-dihydro-2H-pyran (265 mg, 3.150 mmol) in a mixture of THF/CH2Cl2 (1:1, 8 mL). The reaction mixture was stirred for 12 h at room temperature and then the solvent was removed in vacuo. The residue was taken in CH2Cl2 (50 mL) and poured in water (20 mL). The organic layer was separated, the aqueous layer was extracted with CH2Cl2 (50 mL), the combined organic layers were washed with water (40 mL) and brine (40 mL), dried over Na2SO4, and concentrated. Purification by flash chromatography (CH2Cl2) afforded title compound 215 mg (50% yield) as a solid. 1H NMR (400 MHz, CDCl3): δ 10.23 (s, 1H), 9.23 (d, 1H, J=2.0 Hz), 8.35 (dd, 1H, J=2.0 and 9.2 Hz), 7.80 (d, 1H, J=9.2 Hz), 5.89 (dd, 1H, J=2.8 and 8.8 Hz), 3.98 (m, 1H), 3.80 (m, 1H), 2.53 (m, 1H), 2.19 (m, 2H), 1.76 (m, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. additionpoured in water (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL)
  5. washthe combined organic layers were washed with water (40 mL) and brine (40 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-5dda9c52f88a49b3a20b50ba9d976131
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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