Methyl iodide → HCID 67383555, compound

HRID 887888Notes

Reaction equation

HRID 887888 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([OH:17])([CH3:16])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[H-].[Na+].[CH3:22]I>C1COCC1>[F:19][C:2]([F:1])([F:18])[C:3]([O:17][CH3:22])([CH3:16])[CH2:4][N:5]1[C:6](=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]1=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 673836442-(3,3,3-Trifluoro-2-hydroxy-2-methylpropyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67383555HCID 67383555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirring solution of 2-(3,3,3-trifluoro-2-hydroxy-2-methylpropyl)isoindoline-1,3-dione (250 mg, 0.915 mmol)) at 0° C. in THF (8 ml), NaH (80 mg, 2 mmol) was added. After 30 minutes methyl iodide (1.299, 9.15 mmol) was added. The reaction mixture was left stirring in a ice-bath and allowed to warm to 25° C. over 3.5 hours. The reaction was quenched with sat. NH4Cl and the mixture extracted with DCM. The organic extract was separated using a phase seperator and purification by chromatography on silica, eluting in a 0% to 30% iso-hexane:EtOAc afforded the title product; 1H NMR (400 MHz, Methanol-d4) δ 7.91 (2H, m), 7.85 (2H, m), 3.97 (2H, m), 3.44 (3H, s), 1.42 (3H, s);

Workup

  1. waitThe reaction mixture was left
  2. customThe reaction was quenched with sat. NH4Cl
  3. extractionthe mixture extracted with DCM
  4. extractionThe organic extract
  5. customwas separated
  6. customa phase seperator and purification by chromatography on silica
  7. washeluting in a 0% to 30% iso-hexane

Sources & evidence

ORD record
ord-3f34366430034e03adb4bdc2823fdef4
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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