Water → HCID 89862965, compound

HRID 1053675Notes

Reaction equation

HRID 1053675 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].Br[CH2:13][CH2:14][CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26].C([O-])([O-])=O.[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:13][CH2:14][CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 21611N-3-BromopropylphthalimideHCID 679582-Trifluoromethylphenol

Product 1

HCID 89862965HCID 89862965, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-(trifluoromethyl)phenol (250 mg, 1.54 mmol), tetrabutyl ammonium iodide (114 mg, 1.31 mmol) and 2-(3-bromopropyl)isoindoline-1,3-dione (455 mg, 1.70 mmol) was stirred in THF (10 mL) at rt. Cs2CO3 (904 mg, 2.78 mmol) was added. The resulting mixture was stirred at 60° C. for 16 h. H2O was added to the reaction mixture and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by triturating with Et2O to yield Intermediate 6A (0.50 g, 1.4 mmol, 93% yield) as a white powder. LC-MS (ESI) 350 (M+H), RT=3.41 min (Method B).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customby triturating with Et2O

Sources & evidence

ORD record
ord-96e74a2b03544085ac8b8d3ff9c1be94
Source dataset
uspto-grants-2016_07
Patent number
US09394260B2

Reaction notes

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