Pentane → 4-Benzoyl-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine

HRID 1422098Notes

Reaction equation

HRID 1422098 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[C:6]([CH2:13][CH3:14])=[C:5]2[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C([Li])(C)(C)C.CCCCC.CN(C)[C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Cl-].[NH4+]>O1CCCC1>[C:35]([C:2]1[CH:3]=[C:4]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[C:6]([CH2:13][CH3:14])=[C:5]2[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 5

HCID 8003PentaneHCID 11916N,N-DimethylbenzamideHCID 25517Ammonium ChlorideHCID 187069394-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizineHCID 178418306HCID 178418306, compound

Product 1

HCID 187069004-Benzoyl-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizineYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

4-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.345 g, 1.0 mmol), was dissolved in 10 ml of dry tetrahydrofuran under a nitrogen atmosphere, and the solution was cooled to -78° C., while 1.35 M t-butyllithium in pentane (1.5 ml, 2.03 mmol) was added slowly. The orange solution was stirred for 30 minutes at -78° C. N,N-dimethylbenzamide (0.19 g, 1.27 mmol) dissolved in 5 ml of tetrahydrofuran was added and the reaction was stirred for 20 minutes. The reaction mixture was heated to room temperature, and stirred for 2 days. The mixture was poured into 50 ml of a saturated ammonium chloride solution and the organic material was extracted into dichloromethane (4×50 ml). The combined organic layers was washed with brine, dried overmagnesium sulfate, and evaporated to a yellow gum. The crude product was purified by column chromatography over silica gel 60, using 20% of diethyl ether in hexane as the eluent to afford 0.15 g (40%) of 4-benzoyl-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine as a yellow solid. MS(SP): m/z 379 (M+). 1H--NMR (CDCl3, 200 MHz) δ: 1.47 (t, 3 H); 3.21 (q, 2 H); 3.89 (s, 3 H); 7.08 (d, 2 H); 7.46-7.60 (m,3 H); 7.69 (d, 2 H); 7.81-7.98 (m, 5 H); 8.39 (dd, 1 H).

Workup

  1. additionwas added slowly
  2. additionwas added
  3. stirringthe reaction was stirred for 20 minutes
  4. temperatureThe reaction mixture was heated to room temperature
  5. stirringstirred for 2 days
  6. extractionthe organic material was extracted into dichloromethane (4×50 ml)
  7. washThe combined organic layers was washed with brine
  8. dry with materialdried overmagnesium sulfate
  9. customevaporated to a yellow gum
  10. customThe crude product was purified by column chromatography over silica gel 60

Sources & evidence

ORD record
ord-72736569db2644c3a1d7dc58abae2b81
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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