Triethylamine → 1-methyl-6-(3-methyl-3H-imidazol-4-yl)-1H-indole

HRID 651744Notes

Reaction equation

HRID 651744 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:19][N:20]1[C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:23][N:22]=[CH:21]1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:24]3[N:20]([CH3:19])[CH:21]=[N:22][CH:23]=3)[CH:10]=2)[CH:6]=[CH:7]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazoleHCID 155468546-Bromo-1-methyl-1H-indole

Product 1

HCID 155468551-methyl-6-(3-methyl-3H-imidazol-4-yl)-1H-indoleYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 6-bromo-1-methyl-1H-indole (6.2 g, 29.5 mmol) in toluene was degassed by bubbling argon through the solution for 10-20 min. Et3N (8.2 mL, 59 mmol), tetrakis(triphenylphosphine)palladium (0) (681 mg, 0.59 mmol) and 1-methyl-5-(tributylstannyl)imidazole (Gaare, K.; Repstad, T.; Benneche, T.; Undheim, K. Acta Chem. Scan. 1993, 47, 57.) (11.6 g, 31.2 mmol) in toluene (30 mL) were added and the mixture was heated to 120° C. for 18 h until Pd black appeared. The mixture was cooled, filtered through a pad of silica gel and the pad was washed well with EtOAc. The filtrate was evaporated and chromatography of the residue over silica gel using 0.5-1% methanol in EtOAc gave 1-methyl-6-(3-methyl-3H-imidazol-4-yl)-1H-indole (5.21 g, 84%) as an off white crystalline solid.

Workup

  1. customby bubbling argon through the solution for 10-20 min
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a pad of silica gel
  4. washthe pad was washed well with EtOAc
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-60734078521543568c7a828921e219d4
Source dataset
uspto-grants-2001_08
Patent number
US06281356B1

Reaction notes

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