Cesium carbonate → 4-Octylindoline

HRID 710485Notes

Reaction equation

HRID 710485 reaction equation
FC(F)(F)C([N:5]1[C:13]2[C:8](=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CO>[CH2:14]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH2:7][CH2:6][NH:5]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 866618152,2,2-Trifluoro-1-(4-octylindolin-1-yl)ethanone

Product 1

HCID 667295994-OctylindolineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Step C (0.07 g; 0.21 mmol) and Cs2CO3 (0.07 g; 0.21 mmol) in MeOH (2 ml) was stirred overnight at room temperature under N2. After removing solvent under reduced pressure, the residue was diluted to 15 ml with Et2O, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (0.045 g; 93%), as brownish oil, which was used in the next step without further purification. 1H-NMR (CDCl3) 0.86 (m, 3H); 1.28 (m, 10H); 2.47 (m, 2H); 2.95 (m, 2H); 3.52 (m, 2H); 3.7 (broad s, 1H); 6.47-6.54 (m, 2H); 6.89-7.02 (m, 1H).

Workup

  1. customAfter removing solvent under reduced pressure
  2. additionthe residue was diluted to 15 ml with Et2O
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness

Sources & evidence

ORD record
ord-05a4f5eea4844221a40bc8ac32ab01a2
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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