Hydrochloric Acid → HCID 69424087, compound

HRID 350073Notes

Reaction equation

HRID 350073 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:11][CH2:12][O:13][C:14]1[CH:33]=[CH:32][C:17]([CH2:18][N:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([CH:30]=O)=[CH:20]2)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.C(OP([CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])(OCC)=O)C.Cl>CN(C)C=O>[CH3:3][N:4]([CH2:11][CH2:12][O:13][C:14]1[CH:33]=[CH:32][C:17]([CH2:18][N:19]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:21](/[CH:30]=[CH:42]/[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:20]2)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 867604141-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenylpyrrole-3-carbaldehyde

Product 1

HCID 69424087HCID 69424087, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 200.0 mg) was added to a solution of 1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenylpyrrole-3-carbaldehyde (1.35 g) and ethyl diethylphosphonoacetate (1.10 g) in N,N-dimethylformamide (30 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water, then neutralized using 2N hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, then with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatograpy, and ethyl (E)-3-[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]propenoate (1.35 g, yield: 85%) was obtained as an oily substance from the fraction eluted with acetone-hexane (1:2, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b397c247550544c7b3c7e1fa6124813e
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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