p-Toluenesulfonic acid → HCID 67129989, compound

HRID 1038827Notes

Reaction equation

HRID 1038827 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([CH3:11])[CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][O:23]2)=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 247287706-Bromo-4-methyl-1H-indazole

Product 1

HCID 67129989HCID 67129989, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

6-Bromo-4-methyl-1H-indazole (1.0 g, 4.7 mmol, J&W PharmLab) and p-TSA (0.082 g, 0.47 mmol) were dissolved in THF (20 mL). 3,4-Dihydro-2H-pyran (1.99 g, 23.7 mmol) was added and the mixture was heated at about 70° C. for about 6 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (5:1 hexanes:EtOAc) to give 6-bromo-4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.80 g, 41%): LC/MS (Table 2, Method g) Rt=2.28 min; MS m/z: 295, 297 (M+H)1.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography (5:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-0ca82becedad40f08895120baf780d6e
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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