2-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol → 2-[(2-Amino-6-{[2-(2-chlorophenyl)-5-(4-propoxyphenyl)-1H-pyrrol-1-yl]methyl}pyridine-3-yl)oxy]ethanol

HRID 15015Notes

Reaction equation

HRID 15015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:23][C:24]2[N:29]=[C:28]([N+:30]([O-])=O)[C:27]([O:33][CH2:34][CH2:35][OH:36])=[CH:26][CH:25]=2)[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)=[CH:11][CH:12]=1>C(O)C.C(O)(=O)C.C([O-])(O)=O.[Na+].[Fe]>[NH2:30][C:28]1[C:27]([O:33][CH2:34][CH2:35][OH:36])=[CH:26][CH:25]=[C:24]([CH2:23][N:9]2[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=3)=[CH:11][CH:12]=[C:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:29]=1

Participants

5

Reactant 1

HCID 593412002-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol

Product 1

HCID 115837802-[(2-Amino-6-{[2-(2-chlorophenyl)-5-(4-propoxyphenyl)-1H-pyrrol-1-yl]methyl}pyridine-3-yl)oxy]ethanolYield 39%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 516892Sodium BicarbonateSolventHCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
96 °C

Procedure

To a solution of 0.1 gm (0.2 mmol) of 2-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol in 4 mL of 1:1 ethanol-acetic acid was added 0.55 gm of Fe powder. The reaction mixture was allowed to stir at 96° C. for 2 h. The mixture was cooled and poured in 100 mL of saturated NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvents removed under reduced pressure. The residue was purified by column chromatography using 1%-2% methanol-chloroform-0.5% Et3N as an eluent to yield 0.037 gm (39% yield) of a solid mp 89-92° C. 1H NMR (500 MHz, CDCl3) δ: 1.00 (t, 3H, J=7.4 Hz), 1.23 (br s, 3H), 1.77 (m, 2H), 3.88 (m, 4H), 3.98 (t, 2H, J=4.3 Hz), 4.99 (s, 2H), 5.65 (d, 1H, J=8.05 Hz), 6.29 (s, 2H), 6.72 (d, 1H, J=8.05 Hz), 6.84 (d, 1H, J=8.78 Hz), 7.21 (m, 2H), 7.25 (m, 3H), 7.36 (m, 1H); MS (ES) m/z 478.2 ([M+H]+).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customthe solvents removed under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ea38db4250454443b23e0b956ed6b368
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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