Methyl iodide → HCID 86585351, compound

HRID 1356292Notes

Reaction equation

HRID 1356292 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][CH2:19][N:20]=[N+:21]=[N-:22])=[C:15]([Cl:23])[CH:14]=[CH:13][CH:12]=2)[C:5]([O:7][CH3:8])=[O:6].[CH3:25][O-].[Na+].CI>CO>[CH3:1][O:2][C:3](=[O:24])[C:4]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][CH2:19][N:20]=[N+:21]=[N-:22])=[C:15]([Cl:23])[CH:14]=[CH:13][CH:12]=2)([CH3:25])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 86585352HCID 86585352, compound

Product 1

HCID 86585351HCID 86585351, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-[3-(2-azidoethyl)-4-chloro-1H-indol-2-yl]-propanedioic acid dimethyl ester (19.3 mmol) in dry MeOH (0.1 L) at 0° C. under argon was added a 25% NaOMe in MeOH (4.37 mL, 19.11 mmol). The reaction mixture was stirred for 30 min, and MeI (1.82 mL, 29.2 mmol) was added. The mixture was stirred briefly at rt, and then was refluxed overnight. The reaction mixture was concentrated. The residue was taken up with cold H2O. This mixture was extracted with Et2O. The combined Et2O extracts were washed with H2O, dried, filtered, and concentrated to an oil. This oil was purified by silica chromatography to give the title compound: TLC Rf=0.50 (CH2Cl2), MS (ESI+) 387.0; 1H NMR (300 MHz CDCl3) δ 9.95 (1H), 7.27 (1H), 7.07 (2H), 3.83 (6H), 3.48 (2H), 3.15 (2H), 1.94 (3H).

Workup

  1. stirringThe mixture was stirred briefly at rt
  2. temperaturewas refluxed overnight
  3. concentrationThe reaction mixture was concentrated
  4. extractionThis mixture was extracted with Et2O
  5. washThe combined Et2O extracts were washed with H2O
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThis oil was purified by silica chromatography

Sources & evidence

ORD record
ord-f0fab73a79b84a1a9f12cef9d99a91d9
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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