Isopropyl iodide → HCID 69082957, compound

HRID 594736Notes

Reaction equation

HRID 594736 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C:12](=[O:26])[CH:11]([CH3:27])[CH2:10]1.I[CH:29]([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:29]([CH3:31])[CH3:30])[C:3]=1[CH:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=2)[C:12](=[O:26])[CH:11]([CH3:27])[CH2:10]1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69085281HCID 69085281, compound

Product 1

HCID 69082957HCID 69082957, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-fluoro-6-hydroxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one (50 mg; 0.13 mmol), 2-iodopropane (66 mg; 0.39 mmol), potassium carbonate (36 mg; 0.26 mmol), and cesium carbonate (8.5 mg; 0.026 mmol) in anh. DMF (0.7 ml) was stirred at rt, under nitrogen, for 17 h. Subsequent filtration and purification by preparative HPLC afforded the target compound 5-(2-fluoro-6-isopropoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one. LC-MS (conditions A): tR=1.00 min.; [M+H]+: 426.01 g/mol.

Workup

  1. filtrationSubsequent filtration and purification by preparative HPLC

Sources & evidence

ORD record
ord-dc195f8e98fb4612bb7898babd81c07e
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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