Ethyl bromoacetate → HCID 69483666, compound

HRID 1664498Notes

Reaction equation

HRID 1664498 reaction equation
[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([CH:5]1[CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]#[N:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7][CH2:6]1)=[O:4].CC([O-])(C)C.[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].OP([O-])(O)=O.[K+]>CN(C=O)C>[C:18]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:8]1[CH2:7][CH2:6][CH:5]([C:3](=[O:4])[N:2]([CH3:1])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:17][C:16]2=1)#[N:19]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 516951Monobasic potassium phosphateHCID 23665647Potassium tert-butoxideHCID 67359365HCID 67359365, compound

Product 1

HCID 69483666HCID 69483666, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (±)-6-cyano-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid methyl-phenyl-amide (0.14 g, 0.43 mmol) in dry DMF (1.5 ml) is added KOtBu (58 mg, 0.52 mmol) and ethyl bromoacetate (79 mg, 0.47 mmol). The reaction mixture is stirred at rt overnight, then poured into saturated aqueous KH2PO4 and extracted with CH2Cl2. The combined organic layers are washed with H2O and brine, dried over Na2SO4, filtered and evaporated. The residue is purified by column chromatography on silica gel (hexane/EtOAc 1:1) to provide subtitle compound (91 mg) as a beige solid in 51% yield. tR (LC-3) 1.15 min; ESI-MS (positive ion): m/z 416.09 [M+H]+ (calcd 415.19 for C25H25N3O3). 1H-NMR (CDCl3): 1.13 (t, J=7.0 Hz, 3H); 1.79 (m, 1H); 2.05 (m, 1H); 2.25 (m, 1H); 2.65 (m, 1H); 2.72 (m, 2H); 3.19 (s, 3H); 3.24 (m, 1H); 4.07 (q, J=7.0 Hz, 2H); 5.00 (d, J=3.3 Hz, 2H); 7.33 (m, 1H); 7.41 (m, 5H); 7.50 (d, J=8.0 Hz, 1H); 7.87 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic layers are washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column chromatography on silica gel (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-e1e41fd1a13e40c5bcbf8f00c9789742
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

Loading…