2-Methylindole → HCID 4374415, compound

HRID 1455295Notes

Reaction equation

HRID 1455295 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.[OH-].[K+].Br[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=1>C1OCCOCCOCCOCCOCCOC1>[CH3:1][C:2]1[N:3]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 72242-MethylindoleHCID 14797Potassium Hydroxide2×HCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 4374415HCID 4374415, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 2-methylindole (7.60 mmol, 1.00 g) was added 18-crown-6 (60 mg, 0.06 mmol) and subsequently powdered KOH (416 mg, 7.60 mmol) and methyl 4-(bromomethyl)benzoate (1 eq). The reaction was heated to 100° C. for 2 hr, and was added additional KOH (416 mg, 7.60 mmol). The reaction was stirred for another 1 hr. The reaction was cooled and then quenched with HCl and extracted with EtOAc (2×100 mL). The organic layers were collected, dried and concentrated in vacuo. The crude was flashed to yield the desired acid (798 mg, 40%). MS found: (M+H)+=274.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with HCl
  3. extractionextracted with EtOAc (2×100 mL)
  4. customThe organic layers were collected
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5934f96e96b472380803770da808026
Source dataset
uspto-grants-2009_01
Patent number
US07482372B2

Reaction notes

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