1,2,3,4-Tetramethylbenzene → HCID 14914572, compound

HRID 603397Notes

Reaction equation

HRID 603397 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)C=C.[CH3:14][C:15]1C=CC(C)=C(C)[C:16]=1C>>[CH2:16]([C:6]1[C:5]([OH:4])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)[CH:15]=[CH2:14]

Participants

3

Reactant 2

HCID 102631,2,3,4-TetramethylbenzeneHCID 142392305-(prop-2-en-1-yloxy)-1H-indole

Product 1

HCID 14914572HCID 14914572, compoundYield 70%

Conditions

Temperature
190 °C

Procedure

5-(Allyloxy)-1H-indole (514 mg, 2.97 mmol) (Example 53) was dissolved in 1,2,3,4-tetramethylbenzene (2.5 mL), and the reaction mixture was heated at 190° C. for 2 h. The mixture was cooled to rt and sonicated for 30 min. The mixture was then purified by silica gel column chromatography (EtOAc/hexane (v/v)=1:9) to give 361 mg (70%) of the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 3.68 (d, 2H), 5.13 (d, 1H), 5.18 (d, 1H), 6.07 (m, 1H), 6.45 (s, 1H), 6.79 (d, 1H), 7.12-7.18 (m, 2H), 8.06 (br, 1H).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customsonicated for 30 min
  3. customThe mixture was then purified by silica gel column chromatography (EtOAc/hexane (v/v)=1:9)

Sources & evidence

ORD record
ord-7af03456d7264514b8b0923c74b5bd93
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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