Cesium carbonate → Ethyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

HRID 534276

Reaction equation

HRID 534276 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][C:5]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)=[C:30]([C:39]([F:42])([F:41])[F:40])[CH:29]=1>CC(N(C)C)=O>[CH:34]1([C:31]2[CH:32]=[CH:33][C:28]([CH2:27][O:1][C:2]3[CH:10]=[CH:9][C:8]4[NH:7][C:6]5[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][C:5]=5[C:4]=4[CH:3]=3)=[CH:29][C:30]=2[C:39]([F:40])([F:41])[F:42])[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 53345675Ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetateHCID 534026024-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene

Product 1

HCID 53345674Ethyl 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetateYield 124.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a 2 L, 3-necked, round-bottomed flask under nitrogen atmosphere were placed ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (55.85 g, 215 mmol), cesium carbonate (84.2 g, 258 mmol), 4-(chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene (68 g, 259 mmol) in DMA (670 mL). The mixture was stirred for 15 minutes at room temperature and heated at 50° C. overnight. The mixture was cooled down to room temperature and filtered. The filtrate was concentrated under vacuum. Hexanes (400 mL) were added and the mixture was heated to 40° C. to give a dark solution. The solution was cooled down to room temperature over the weekend. The mixture was concentrated in vacuo and dried under vacuum to give the title compound (129.7 g). LCMS m/z=486.2.

Workup

  1. customIn a 2 L, 3-necked, round-bottomed flask under nitrogen atmosphere were placed
  2. temperatureheated at 50° C. overnight
  3. temperatureThe mixture was cooled down to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. additionHexanes (400 mL) were added
  7. temperaturethe mixture was heated to 40° C.
  8. customto give a dark solution
  9. temperatureThe solution was cooled down to room temperature over the weekend
  10. concentrationThe mixture was concentrated in vacuo
  11. customdried under vacuum

Sources & evidence

ORD record
ord-40535e3690c845dcacb85ecaf5c87a40
Source dataset
uspto-grants-2014_10
Patent number
US08853419B2

Linked notes

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