Cesium carbonate → Ethyl 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423290Notes

Reaction equation

HRID 423290 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[NH:26][CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[N:26]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68320Ethyl 3-bromopropionate2×HCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

Product 1

HCID 59318376Ethyl 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indole (D2) (600 mg), ethyl 3-bromopropanoate (374 μl), caesium carbonate (950 mg) and DMF were heated at 140° C. for 1 hour in a microwave reactor. A further 1 eq. of ethyl 3-bromopropanoate (187 μl) was added and the mixture heated for 30 minutes. The reaction mixture was then evaporated, dissolved in DCM and filtered to give the title compound (650 mg) as a brown solid. δH (CDCl3, 400 MHz): 1.21 (3H, t), 2.85 (2H, t), 4.13 (2H, q), 4.50 (2H, t), 6.61 (1H, d), 7.22 (1H, d), 7.44-7.52 (6H, m), 7.89-7.92 (1H, m), 7.98-8.02 (1H, m), 8.45-8.46 (1H, m). MS (ES): C26H20F3N3O3S requires 511; found 512 (MH+).

Workup

  1. temperaturethe mixture heated for 30 minutes
  2. customThe reaction mixture was then evaporated
  3. dissolutiondissolved in DCM
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4beb20aadc904da2ba6dde9e5d07d5ea
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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