Methyl iodide → HCID 67383555, compound

HRID 444954Notes

Reaction equation

HRID 444954 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 separator 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 separator and purification by chromatography on silica
  7. washeluting in a 0% to 30% iso-hexane

Sources & evidence

ORD record
ord-fba7ab7898364fe7a043d6cd1a79e490
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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