Cesium carbonate → tert-Butyl 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515698Notes

Reaction equation

HRID 515698 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]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[C:32]([C:43]([F:46])([F:45])[F:44])[CH:31]=1>CC(N(C)C)=O>[CH:37]1([CH2:36][C:33]2[CH:34]=[CH:35][C:30]([CH2:29][O:1][C:2]3[CH:10]=[CH:9][C:8]4[N:7]5[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]5=[CH:5][C:4]=4[CH:3]=3)=[CH:31][C:32]=2[C:43]([F:44])([F:45])[F:46])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 672491474-(Chloromethyl)-1-(cyclohexylmethyl)-2-(trifluoromethyl)benzeneHCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 67250595tert-Butyl 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateYield 62.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.045 g, 0.157 mmol) in DMA (1 mL) was added Cs2CO3 (0.0.077 g, 0.235 mmol) followed by 4-(chloromethyl)-1-(cyclohexylmethyl)-2-(trifluoromethyl)benzene (0.050 g, 0.172 mmol). The reaction was stirred at 60° C. for 16 h. The mixture was filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography to give the title compound as a white solid (0.053 g). LCMS m/z=542.5 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90-1.03 (m, 2H), 1.09-1.19 (m, 3H), 1.44 (s, 9H), 1.53-1.69 (m, 6H), 2.14-2.26 (m, 1H), 2.51-2.58 (m, 1H), 2.59-2.67 (m, 3H), 2.71-2.81 (m, 1H), 3.53-3.63 (m, 1H), 3.91-3.99 (m, 1H), 4.05-4.14 (m, 1H), 5.12 (s, 2H), 5.99 (s, 1H), 6.77 (dd, J=8.72, 2.40 Hz, 1H), 7.07 (d, J=2.40 Hz, 1H), 7.19 (d, J=8.72 Hz, 1H), 7.44 (d, J=7.96 Hz, 1H), 7.65 (d, J=7.96 Hz, 1H), 7.73 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated under vacuum
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-cc12f2305a6b4df5af5e21f88a3f3e91
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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