Methyl iodide → HCID 59596237, compound

HRID 2264715Notes

Reaction equation

HRID 2264715 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27](Br)[CH:26]=2)([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].IC.C(OCC)(=O)C>CN(C)C=O>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 59596300HCID 59596300, compound

Product 1

HCID 59596237HCID 59596237, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of [3,3-bis-(4-hydroxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, C) (5.0 g, 12.0 mmol) and cesium carbonate (3.9 mL, 12.0 mmol) in N,N-dimethyl formamide (100 mL) was added iodomethane (0.7 mL, 11.4 mmol) in N,N-dimethyl formamide (3 mL) and the mixture stirred at ambient temperature for 18 hours. The N,N-dimethyl formamide was removed under reduced pressure to yield an amber syrup. To this was added ethyl acetate (250 mL) and the mixture stirred vigorously for 0.5 h. The insolubles were filtered and the filtrate concentrated under reduced pressure to yield a tan solid. The crude compound was purified using flash chromatography (silica; 90:10 dichloromethane:ethyl acetate) to give the title compound as a white solid (2.11 g, 34%). 1H NMR (300 MHz, DMSO-d6) δ 7.83 (d, J=7.5 Hz, 1 H), 7.64 (t, J=7.3 Hz, 1 H), 7.55-7.49 (m, 2 H), 7.16 (d, J=8.8 Hz, 2 H), 7.04 (d, J=8.6 Hz, 2 H), 6.89 (d, J=8.8 Hz, 2 H), 6.71 (d, J=8.7 Hz, 2 H), 3.71 (d, J=8.3 Hz, 3 H), 1.46 (s, 9 H); MS (APCI+) m/z 430 [M+1]+; tR=2.20 min.

Workup

  1. customThe N,N-dimethyl formamide was removed under reduced pressure
  2. customto yield an amber syrup
  3. stirringthe mixture stirred vigorously for 0.5 h
  4. filtrationThe insolubles were filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto yield a tan solid
  7. customThe crude compound was purified

Sources & evidence

ORD record
ord-1430c936d0db43fba505e3a0f36dd5e3
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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