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

HRID 423335Notes

Reaction equation

HRID 423335 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].[CH2:12]([O:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18]Br)[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)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[CH2:18][CH2:17][CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:20])#[N:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrateHCID 38176024-Cyanoindole

Product 1

HCID 59318426Ethyl 4-(4-cyano-1H-indol-1-yl)butanoateYield 91.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combined 4-cyanoindole (5 g, 35.2 mmol), ethyl-4-bromobutanoate (10.29 g, 52.8 mmol) and cesium carbonate (22.92 g, 70.3 mmol) and heated to 80° C. under argon for 1 hour. The reaction was allowed to cool and then 150 ml diethyl ether was added and the organic solution was washed with 3×150 ml H2O. Dried the organic solution over MgSO4 and evaporated the solvent. Dried on high vacuum over the weekend to afford the title compound (8.25 g) as an orange oil. δH (400 MHz, d6-DMSO). 1.13 (3H, t), 1.96-2.05 (2H, m), 2.26 (2H, t), 3.99 (2H, q), 4.29 (2H, t), 6.60 (1H, dd), 7.29 (1H, apparent t), 7.55 (1H, dd), 7.68 (1H, d), 7.90 (1H, d). MS (ES): C15H16N2O2 requires 256; found 257 (MH+).

Workup

  1. temperatureto cool
  2. washthe organic solution was washed with 3×150 ml H2O
  3. dry with materialDried the organic solution over MgSO4
  4. customevaporated the solvent
  5. customDried on high vacuum over the weekend

Sources & evidence

ORD record
ord-9a0ac43e7ab2436da56ac42a5eba9fd0
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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