Methyl iodide → HCID 59783536, compound

HRID 1946636Notes

Reaction equation

HRID 1946636 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]1[CH2:17][CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1.[CH3:30]I>CC(C)=O>[CH3:30][N:11]1[CH2:10][CH2:9][C:8]2[C:2](=[O:1])[N:3]([CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=3)[C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[O:6][C:7]=2[CH2:12]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59783670HCID 59783670, compound

Product 1

HCID 59783536HCID 59783536, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Title compound 448 (0.249 g, 0.638 mmol) was solubilized in acetone (15.0 mL) and the methyl iodide (2.0 mL) was added. The reaction mixture was stirred in a sealed tube at 60° C. for 18 hours. The mixture was cooled down and evaporated. The residue was dissolved in methanol (15 mL) and Pt black (55 mg) was added. The reaction mixture was stirred over 55PSI of hydrogen for 3 hours. The catalyst was filtered and the filtrate was evaporated. The crude was purified by flash chromatography (75-100% ethyl acetate in hexanes with 1.5% of ammonium hydroxide) to afford title compound 452 (133 mg, 51%). 1H NMR (DMSO-d6) δ (ppm): 7.89 (d, J=8.2 Hz, 2H), 7.54 (d, J=8.0 Hz, 1H), 7.26 (t, J=7.7 Hz, 1H), 7.19 (t, J=7.7 Hz, 1H), 7.07 (dd, J=7.4, 1.2 Hz, 1H), 6.88 (d, J=8.2 Hz, 2H), 4.38 (t, J=4.9 Hz, 2H), 4.31 (t, J=4.9 Hz, 2H), 3.84 (s, 3H), 3.17 (s, 2H), 2.52-2.51 (m, 2H), 2.44 (m, 2H), 2.36 (s, 3H). MS (m/z): 409.4 (M+H).

Workup

  1. temperatureThe mixture was cooled down
  2. customevaporated
  3. dissolutionThe residue was dissolved in methanol (15 mL)
  4. additionPt black (55 mg) was added
  5. stirringThe reaction mixture was stirred over 55PSI of hydrogen for 3 hours
  6. filtrationThe catalyst was filtered
  7. customthe filtrate was evaporated
  8. customThe crude was purified by flash chromatography (75-100% ethyl acetate in hexanes with 1.5% of ammonium hydroxide)

Sources & evidence

ORD record
ord-fe3a117a09714c8cb78f42dd450338cf
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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