Methyl iodide → HCID 68283810, compound

HRID 1527264Notes

Reaction equation

HRID 1527264 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:20])[CH3:19])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22]([O-])([O-])=O.[K+].[K+].IC>CC#N>[C:1]([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:22])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:20])[CH3:19])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 68283428HCID 68283428, compound

Product 1

HCID 68283810HCID 68283810, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3-acetyl-5-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (500 mg, 1.73 mmol) in CH3CN (15 mL) was added K2CO3 (358 mg, 2.59 mmol) and iodomethane (0.162 mL, 2.59 mmol). The reaction mixture was stirred at 50° C. overnight. Additional K2CO3 (716 mg, 5.18 mmol) and iodomethane (0.324 mL, 5.18 mmol) were added and heating was continued for an additional 2 days. Volatiles were evaporated, the reaction mixture was taken up in water and extracted twice with AcOEt. The combined organic phases were dried (Phase separator) and evaporated to give the title compound. MS (LC/MS): 304.0 [M+H]+, 629.0 [2M+Na]+; tR (HPLC conditions c): 4.92 min.

Workup

  1. temperatureheating
  2. waitwas continued for an additional 2 days
  3. customVolatiles were evaporated
  4. extractionextracted twice with AcOEt
  5. customThe combined organic phases were dried (Phase separator)
  6. customevaporated

Sources & evidence

ORD record
ord-94f9db5592364bab9bc63c4ac6e72212
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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