Cesium carbonate → HCID 67250244, compound

HRID 1964107Notes

Reaction equation

HRID 1964107 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH:37]([CH3:39])[CH3:38])=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=1>CN(C=O)C>[CH2:36]([C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:1][C:2]2[CH:10]=[CH:9][C:8]3[N:7]4[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]4=[CH:5][C:4]=3[CH:3]=2)=[CH:31][C:32]=1[C:40]([F:41])([F:42])[F:43])[CH:37]([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 58020731HCID 58020731, compoundHCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 67250244HCID 67250244, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.04 g, 0.139 mmol) was dissolved in DMF (1.0 mL) and cesium carbonate (0.045 g, 0.139 mmol) and 4-(chloromethyl)-1-isobutyl-2-(trifluoromethyl)benzene (0.035 g, 0.139 mmol) was added. The reaction mixture was stirred at room temperature for 48 h and then filtered through Celite®. The filtrate was partitioned between EtOAc and water. The aqueous layer was extracted two additional times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the title compound (58 mg). LCMS m/z=502.6 [M+H]+.

Workup

  1. filtrationfiltered through Celite®
  2. customThe filtrate was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted two additional times with EtOAc
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8664169ecbc44e1c8c010bfaf1950505
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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