Cesium carbonate → Ethyl 3-(4-cyano-1H-indol-1-yl)propanoate

HRID 423334Notes

Reaction equation

[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Cyanoindole (2.5 g) was dissolved in DMF (7.5 ml). Cs2CO3 (11.46 g) was added followed by ethyl 3-bromopropionate (3.38 ml). This mixture was heated to 80° C. for 40 minutes. A further portion of DMF (5 ml) was added and heating at 80° C. continued for 1 hour. The reaction mixture was evaporated then dissolved in H2O (200 ml) and extracted with EtOAc (200 ml). This was evaporated to give a yellow oil (3.5 g) which was purified on a 40+M Biotage cartridge, eluting with a 25-75% mixture of Et2O in hexane. This gave the title compound (3.44 g) as a pale yellow oil. δH (CDCl3, 400 MHz): 1.19 (3H, t), 2.82 (2H, t), 4.12 (2H, q), 4.50 (2H, t), 6.71 (1H, d), 7.23-7.28 (1H, m), 7.33 (1H, d), 7.47 (1H, d), 7.60 (1H, dd). MS (ES): C14H14N2O2 requires 242; found 243 (MH+).

Workup

temperatureheating at 80° C.
customThe reaction mixture was evaporated
dissolutionthen dissolved in H2O (200 ml)
extractionextracted with EtOAc (200 ml)
customThis was evaporated

Sources & evidence

ORD record: ord-d5514c7db0a14e3e956edd52cdb1d50f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101775B2

Reaction notes

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