5-Benzyloxyindole → (5-Benzyloxyindole-1-yl)acetic acid methyl ester

HRID 2424933Notes

Reaction equation

HRID 2424933 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CN(C=O)C>[CH3:25][O:24][C:22](=[O:23])[CH2:21][N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13]1

Participants

5

Reactant 3

HCID 146245-BenzyloxyindoleHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 20770836(5-Benzyloxyindole-1-yl)acetic acid methyl esterYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-benzyloxyindole (1.67 g, 7.489 mmol) in DMF (50 mL) was added sodium hydride (60% dispersion in mineral oil, 389 mg, 9.735 mmol). The resulting suspension was stirred at rt for 1 h at which time methyl bromoacetate (1.26 g, 8.238 mmol) was added. The resulting solution was stirred at rt for 4.5 h. The reaction was quenched with sat. aqueous ammonium chloride solution (25 mL), and diluted with EtOAc (50 mL). The organic layer was washed three times with water. The aqueous layer was extracted with EtOAc again and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated via rotary evaporation. The resulting brown oil was purified on silica gel (hexanes/EtOAc 1:1) to give the title compound as a brownish oil (1.64 g, 74%). LC/MS m/z 296 (M+H)+, RT 3.21 min; 1H NMR (400 MHz, CDCl3) δ 7.35-7.37 (m, 2H), 7.23-7.30 (m, 3H), 7.02-7.08 (m, 2H), 6.95 (d, 1H), 6.87 (dd, 1H), 6.37 (dd, 1H), 5.01 (s, 2H), 4.72 (s, 2H), 3.64 (s, 3H).

Workup

  1. additionwas added
  2. customThe reaction was quenched with sat. aqueous ammonium chloride solution (25 mL)
  3. additiondiluted with EtOAc (50 mL)
  4. washThe organic layer was washed three times with water
  5. extractionThe aqueous layer was extracted with EtOAc again
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated via rotary evaporation
  9. customThe resulting brown oil was purified on silica gel (hexanes/EtOAc 1:1)

Sources & evidence

ORD record
ord-6b59ffdc095d4cb39f248aae92cf5b14
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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