2-Methylindole → HCID 69301089, compound

HRID 1297264Notes

Reaction equation

HRID 1297264 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]Br.CN1CCCC1=O>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 72242-MethylindoleHCID 11430Potassium CarbonateHCID 5196711-(Benzyloxy)-4-iodobenzene

Product 1

HCID 69301089HCID 69301089, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To a mixture of 2-methylindole (3.28 g, 25 mmol), 4-benzyloxy iodobenzene (7.76 g, 25 mmol), potassium carbonate (2.65 g, 25 mmol), and N-methylpyrrolidinone (250 mL) was added copper (I) bromide (0.5 g, 3.5 mmol). The stirred solution was heated to 180° C. and maintained for 18 hr. The reaction mixture was cooled, poured onto ice and extracted with ethyl acetate. After washing the organic layer with water and brine, and drying over anhydrous MgSO4 the solvent was removed to yield a dark liquid. Purification by silica gel chromatography (2% ethyl acetate-hexanes) provided the title compound as a white solid (30%): mp 95-96° C.; 1H NMR (DMSO-d6): δ 2.24 (3H, s), 5.19 (2H, s), 6.38 (1H, s), 6.93-7.04 (3H, m), 7.20 (2H, d, J=11.9 Hz), 7.23 (2H, d, J=3.1Hz), 7.32-7.53 (8H, m); MS m/z (M+H)+ 314: Anal. for C22H19NO 0.1H2O: Calc'd: C, 83.83; H, 6.14; N, 4.44. Found: C, 83.84; H, 6.18; N, 4.29.

Workup

  1. temperaturemaintained for 18 hr
  2. temperatureThe reaction mixture was cooled
  3. additionpoured onto ice
  4. extractionextracted with ethyl acetate
  5. washAfter washing the organic layer with water and brine
  6. dry with materialdrying over anhydrous MgSO4 the solvent
  7. customwas removed
  8. customto yield a dark liquid
  9. customPurification by silica gel chromatography (2% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-4fcdb1b266604472badc655625dbe9e5
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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