Benzyl Bromide → HCID 71284415, compound

HRID 1481762Notes

Reaction equation

HRID 1481762 reaction equation
[OH:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:15].C([O-])([O-])=O.[K+].[K+].[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1>CC#N.[Na+].[I-]>[CH2:28]([O:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:15])[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5274452HCID 5274452, compound

Product 1

HCID 71284415HCID 71284415, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-hydroxy-1-methyl-1H-indole-5-carboxylate (7.70 g, 37.52 mmol), prepared according to the literature (Bioorg. Med. Chem. 2005, 13, 1497-1505), in CH3CN (150 mL) was added K2CO3 (8.80 g, 63.67 mmol), NaI (200 mg, cat.) and BnBr (6.70 mL, 56.41 mmol). The mixture was heated at 70° C. overnight. The solids were filtered off and the mother liquor was concentrated. The residue was purified by column chromatography using EtOAc/hexanes (gradient 10-30%) to afford methyl 4-(benzyloxy)-1-methyl-1H-indole-5-carboxylate (7.10 g) in 85% yield based on recovered starting material (1.90 g).

Workup

  1. filtrationThe solids were filtered off
  2. concentrationthe mother liquor was concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-50f2e46e3af545cc88b34b0ae0559e27
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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