Methyl iodide → HCID 57429429, compound

HRID 1640021Notes

Reaction equation

HRID 1640021 reaction equation
[OH:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[CH:16][CH:17]=3)[C:12]2=[O:22])=[CH:7][CH:6]=1)[CH3:4].I[CH3:24]>C(#N)C.O.C(OCC)(=O)C.[Ag]=O>[CH3:21][O:20][C:15]1[CH:14]=[C:13]2[C:18]([CH2:19][N:11]([C:8]3[CH:7]=[CH:6][C:5]([CH:3]([CH3:4])[CH2:2][O:1][CH3:24])=[CH:10][CH:9]=3)[C:12]2=[O:22])=[CH:17][CH:16]=1

Participants

7

Reactant 2

HCID 6328Methyl iodideHCID 57429430HCID 57429430, compound

Product 1

HCID 57429429HCID 57429429, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-(1-hydroxypropan-2-yl)phenyl)-6-methoxyisoindolin-1-one (0.042 g, 0.14 mmol), silver oxide (0.196 g, 0.42 mmol), iodomethane (0.070 mL) and 4 Å molecular sieves (0.050 g) in acetonitrile (2 mL) was stirred for 96 h at room temperature. After this time, the mixture was diluted with water (10 mL) and ethyl acetate (10 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an off-white solid Purification by flash chromatography (silica, 1:1 ethyl acetate/hexanes) afforded 6-methoxy-2-(4-(1-methoxypropan-2-yl)phenyl)isoindolin-1-one (0.031 g, 72%) as a white solid: mp 116-118° C.; 1H NMR (300 MHz, CDCl3) δ 7.78 (dd, J=8.7, 2.0 Hz, 2H), 7.40-7.38 (m, 2H), 7.29 (dd, J=8.6, 1.9 Hz, 2H), 7.15 (dd, J=8.3, 2.4 Hz, 1H), 4.78 (m, 2H), 3.89 (s, 3H), 3.55-3.41 (m, 2H), 3.34 (s, 3H), 3.04 (q, J=7.0 Hz, 1H), 1.29 (d, J=7.0 Hz, 3H); ESI MS m/z 312 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford
  6. customan off-white solid Purification by flash chromatography (silica, 1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cdc0c0f4209a410b876566a3a2fe9c2d
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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