Water → HCID 69584895, compound

HRID 322045Notes

Reaction equation

HRID 322045 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-64e4d349e6f24a849275c42b50828a74
Source dataset
uspto-grants-2001_04
Patent number
US06211208B1

Reaction notes

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