Pyridine → HCID 18707043, compound

HRID 1422095Notes

Reaction equation

HRID 1422095 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[N:11]2[C:12]=1[C:13]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)=[C:14]3[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].C(=O)([O-])O.[Na+]>O1CCCC1>[C:34]([O:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[C:12]3=[C:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=[C:10]4[N:11]3[C:15](=[CH:16][CH:17]=[CH:18]4)[C:14]=2[CH2:19][CH3:20])=[CH:22][CH:23]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 18706943HCID 18706943, compound

Product 1

HCID 18707043HCID 18707043, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Benzyl-1-ethyl-2-(4-hydroxyphenyl)pyrrolo[2,1,5-cd]indolizine (143 mg, 0.66 mmol) was dissolved in 10 ml of dry tetrahydrofuran and -.10 ml of dry pyridine and acetic anhydride (0.6 ml, 5.43 mmol) was added. The mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into 100 ml of saturated sodium hydrogen carbonate and stirred for 20 minutes. The organic material was extracted into dichloromethane (4×50 ml), and the combined organic layers were washed with brine, dried over magnesium sulfate and the solvent was evaporated. The crude product was purified by column chromatography over silica gel 60, using 5% of diethyl ether in petroleum ether as the eluent to afford 91 mg (35%) of 2-(4-acetoxyphenyl)-3-benzyl-1-ethylpyrrolo[2,1,5-cd]indolizine as a solid. MS(SP): m/z 393 (M+). 1H-NMR (CDCl3, 300 MHz) δ: 1.39 (t, 3H); 2.37 (s, 3H); 3.10 (q, 2H); 4.29 (s, 2H); 6.94 (s, 1H); 7.05-7.25 (m, 7H); 7.52 (d, 2H); 7.61 (dd, 1H); 7.80 (d, 1H), 7.89 (d, 1H).

Workup

  1. stirringstirred for 20 minutes
  2. extractionThe organic material was extracted into dichloromethane (4×50 ml)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe crude product was purified by column chromatography over silica gel 60

Sources & evidence

ORD record
ord-4ad420a91f2e4168ab9cc1df71e2e61c
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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