Potassium Carbonate → HCID 86670928, compound

HRID 515267Notes

Reaction equation

HRID 515267 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[N+:19]([C:22]1[CH:33]=[CH:32][C:25]([O:26][CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)=[CH:24][CH:23]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:11][C:10]([F:13])([F:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:29]2[CH2:30][CH2:31][CH:27]([O:26][C:25]3[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:33][CH:32]=3)[CH2:28]2)=[CH:4][CH:5]=1)([OH:18])[C:14]([F:17])([F:16])[F:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219186903-(4-Nitrophenoxy)pyrrolidineHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86670928HCID 86670928, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (9.61 mmol, 4.63 mL, 3.24 g), 3-(4-nitrophenoxy)pyrrolidine (9.61 mmol, 2 g) and potassium carbonate (19.21 mmol, 2.65 g) were combined and stirred at room temperature in acetonitrile (50 mL) for 1 hour. The reaction mixture was filtered and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: dichloromethane to 15% methanol in dichloromethane) and SCX chromatography to afford the intermediate 1,1,1,3,3,3-hexafluoro-2-(4-((3-(4-nitrophenoxy)pyrrolidin-1-yl)methyl)phenyl)propan-2-ol (750 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by silica column chromatography (eluent: dichloromethane to 15% methanol in dichloromethane) and SCX chromatography

Sources & evidence

ORD record
ord-68b687dc1a3e4758a38e349033fcb441
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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