4-Bromotoluene → HCID 71567673, compound

HRID 128992Notes

Reaction equation

HRID 128992 reaction equation
[C:1]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2].Br[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1>N1C=CC=CC=1.C(OCC)(=O)C.[Cu-]=O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[C:6]2[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 78054-BromotolueneHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 71567673HCID 71567673, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2-Carboethoxy-indole (100 mg, 0.528 mmol, 1.0 eq.) was combined with 4-bromotoluene (0.16 ml, 1.32 mmol, 2.5 eq.) and copper(I) oxide (75.6 mg, 0.528 mmol, 1.0 eq.) in pyridine (0.53 ml, 1M) and heated at 120° C. for 2 hours. The reaction was then cooled to room temperature, diluted with ethyl acetate and filtered through celite. The filtrate was washed twice with water, twice with 1N hydrochloric acid and once with aqueous saturated sodium hydrogen carbonate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on silica gel, eluting with chloroform:hexane (1:2) to give the title A compound (147.6 mg).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationfiltered through celite
  3. washThe filtrate was washed twice with water, twice with 1N hydrochloric acid and once with aqueous saturated sodium hydrogen carbonate
  4. filtrationfiltered through magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with chloroform:hexane (1:2)

Sources & evidence

ORD record
ord-3c63f5626fbb424e85a20698ba8e1062
Source dataset
uspto-grants-1995_11
Patent number
US05466704

Reaction notes

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