Methyl iodide → HCID 67383555, compound

HRID 2202541Notes

Reaction equation

HRID 2202541 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); LC-MS: Rt 1.17 min; MS m/z 288.10 [M+H]+; Method 2minLC_v003.

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-540be305bdc3484db651fcf63e3bbe3a
Source dataset
uspto-grants-2016_06
Patent number
US09365552B2

Reaction notes

Loading…