4-Bromotoluene → HCID 66661168, compound

HRID 1047648Notes

Reaction equation

HRID 1047648 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.Br[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.CN[C@H]1[C@H](NC)CCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.C1(C)C=CC=CC=1>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=3)[CH:3]=[CH:2]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 78054-BromotolueneHCID 62657Potassium Phosphate, TribasicHCID 639844Methyl indole-6-carboxylateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 66661168HCID 66661168, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

To a mixture of methyl indole-6-carboxylate (2.03 g, 11.6 mmol), 4-bromotoluene (3.56 g, 20.8 mmol), trans-(1R,2R)—N,N′-bismethyl-1,2-cyclohexane diamine (0.18 mL, 1.14 mmol), copper iodide (0.12 g, 0.60 mmol) and tribasic potassium phosphate (5.50 g, 25.9 mmol) was added toluene (11.5 mL). The mixture was heated in a sealed tube at 180° C. for 10 min. The mixture was cooled to ambient temperature, filtered with Celite and concentrated under reduced pressure. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (1.48 g): LC-MS [M+1]=266.1.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered with Celite
  3. concentrationconcentrated under reduced pressure
  4. customPurification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5a9a02cd5c7746768a07a18570a690c3
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

Loading…