Water → HCID 69584895, compound

HRID 842047Notes

Reaction equation

HRID 842047 reaction equation
C(N(CC)[CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]([C:20]2[N:25]=[C:24](N)[CH:23]=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)C.BrCC(O[CH2:34][CH3:35])=O.C(=O)([O-])[O-].[K+].[K+].[OH2:42]>C(#N)C>[CH3:21][C:20]1[NH:25][C:34]([CH3:35])=[CH:12][C:13]=1[C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([C:13]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:19]=3[C:10]([O:9][CH2:8][C:7]([O:6][CH2:5][CH3:4])=[O:42])=[CH:11][CH:12]=2)[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15524290HCID 15524290, compound

Product 1

HCID 69584895HCID 69584895, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared from 2-(2,5-dimethylpyrrolyl)-6-[4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl]-pyridine (from Example 1) by alkylation with ethyl bromoacetate, using potassium carbonate, in acetonitrile. The mixture was refluxed 12 hours, cooled, poured into water, and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to an 83.5% yield of the product as an oil. 1H-NMR (δ, CDCl3): 1.31 (t, J=7, 3H), 1.71 (m, 2H), 1.83 (m, 2H), 2.19 (s, 6H), 4.26 (q, J=7, 2H), 4.66 (s, 2H), 5.90 (s, 2H), 6.64 (d, J=8, 1H), 7.12 (d, J=8, 1H), 7.20 (d, J=8, 1H), 7.35 (d, J=8, 1H), 7.82 (t, J=8, 1H); 13C-NMR (δ, CDCl3): 13.4, 14.2, 22.3, 22.9, 23.7, 28.7, 61.2, 65.5, 106.7, 107.8, 119.6, 123.0, 126.9, 127.7, 128.5, 133.4, 137.0, 138.1, 151.3, 156.0, 160.1, 169.0; MS (%): 405 (parent+1, 100).

Workup

  1. temperatureThe mixture was refluxed 12 hours
  2. temperaturecooled
  3. extractionextracted into ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0c144677acb2417bad9ebd57f4c071f9
Source dataset
uspto-grants-2002_04
Patent number
US06372768B1

Reaction notes

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