Cesium carbonate → HCID 67248467, compound

HRID 1964094Notes

Reaction equation

HRID 1964094 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]3[CH2:10][CH2:11][CH:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]3=[N:7][C:6]=2[CH:19]=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>CN(C=O)C.O>[CH:34]1([C:31]2[CH:32]=[CH:33][C:28]([CH2:27][O:1][C:2]3[CH:3]=[CH:4][C:5]4[N:9]5[CH2:10][CH2:11][CH:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]5=[N:7][C:6]=4[CH:19]=3)=[CH:29][C:30]=2[C:39]([F:40])([F:41])[F:42])[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 534026024-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzeneHCID 67248313Ethyl 2-(6-Hydroxy-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate

Product 1

HCID 67248467HCID 67248467, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(6-hydroxy-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate (0.1 g, 0.384 mmol) was dissolved in DMF (1.0 mL) and cesium carbonate (0.150 g, 0.461 mmol) and 4-(chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene (0.111 g, 0.423 mmol) were added. The reaction mixture was stirred at room temperature for 1.5 h and then warmed to 40° C. After stirring for 1 h, the reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to provide the title compound (126 mg). LCMS m/z=487.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (t, J=7.2 Hz, 3H), 1.55-1.65 (m, 2H), 1.67-1.78 (m, 2H), 1.81-1.91 (m, 2H), 2.04-2.14 (m, 2H), 2.36-2.47 (m, 1H), 2.62 (dd, J=16.4, 9.7 Hz, 1H), 2.97-3.07 (m, 1H), 3.16 (dd, J=16.8, 3.8 Hz, 1H), 3.33-3.43 (m, 1H), 3.64-3.74 (m, 1H), 3.97-4.05 (m, 1H), 4.09-4.21 (m, 3H), 5.09 (s, 2H), 6.87 (d, J=2.4 Hz, 1H), 6.93 (dd, J=8.6, 2.4 Hz, 1H), 7.49 (d, J=8.3 Hz, 1H), 7.56-7.61 (m, 2H), 7.68 (s, 1H).

Workup

  1. temperaturewarmed to 40° C
  2. stirringAfter stirring for 1 h
  3. extractionextracted three 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 column chromatography

Sources & evidence

ORD record
ord-bb2b1def3174452c83c880ac5cbbc45d
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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