p-Toluenesulfonic acid → HCID 86728242, compound

HRID 1776833Notes

Reaction equation

HRID 1776833 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1.[CH3:18][C:19]1C=CC(S(O)(=O)=O)=C[CH:24]=1>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[C:19]([CH3:24])([CH3:18])[O:8][C:5]2=[CH:6][CH:7]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13163448HCID 13163448, compound

Product 1

HCID 86728242HCID 86728242, compoundYield 391.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
150 °C

Procedure

To the solution of 4-bromo-2-(1H-indol-2-yl)phenol (200 mg, 0.69 mmol) in acetone (5 mL) was added PTSA (26 mg, 0.14 mmol), it was stirred at 150° C. in a sealed tube. Then the solvent was removed and the crude product was purified using prep-TLC to provide the desired product of 2-bromo-6,6-dimethyl-6,11-dihydrochromeno[4,3-b]indole (180 mg, yield: 79.3%). MS (M+H)+: 327/329.

Workup

  1. customThen the solvent was removed
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-504ee3965bda4e8c96961e0d04b2ba5d
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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