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

HRID 1422100Notes

Reaction equation

HRID 1422100 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(=O)([O-])[O-].[Na+].[Na+].O.[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COCCOC>[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][C:41]([C:2]2[CH:3]=[C:4]3[N:12]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=24)[C:6]([CH2:13][CH3:14])=[C:5]3[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 187069394-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine

Product 1

HCID 187070174-(4-Benzyloxyphenyl)-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizineYield 68%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
87.5 °C

Procedure

4-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.354 g, 1.0 mmol), prepared in example 75, step 2, was dissolved in 15 ml of 1,2-dimethoxyethane under a nitrogen atmosphere. tetrakistriphenylphospine palladium(0) (0.06 g, 0.052 mmol) was added, and the mixture was stirred for 10 minutes. Sodium carbonate (0.65 g, 6.13 mmol) and water 2 ml was added and stirring was continued for 10 minutes. 4-Benzyloxyphenyl boronic acid (0.91 g, 3.99 mmol) dissolved in 10 ml of hot 1,2-dimethoxyethane was added and the mixture was heated to 85-90° C. for 18 hours. The suspension was poured into 100 ml of water and the organic material was extracted into dichloromethane (1×100 ml and 3×50 ml). The combined organic layers were washed with brine, dried overmagnesium sulfate, and evaporated. The crude product was purified by column chromatography over silica gel 60, using 3% of diethyl ether in hexane as the eluent to afford a yellow solid, which was recrystallised from dichloromethane and petroleum ether, to afford 0.31 g (68%) of 4-(4-benzyloxyphenyl)-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine as yellow crystals. MS(SP): m/z 457 (M+). 1H--NMR (CDCl3, 400 MHz) δ: 1.48 (t, 3 H); 3.25 (q, 2 H); 3.91 (s, 3 H); 5.14 (s, 2 H); 7.07-7.13 (m,4 H); 7.31-7.51 (m, 5 H); 7.67 (dd, 1 H); 7.70 (s, 1 H); 7.73-7.82 (m, 4 H); 7.92 (d, 1 H); 8.13 (d, 1 H). Analysis: Calculated for C32H27N1O2 : C, 84.00; H, 5.95; N, 3.06%; Found: C, 84.07; H, 6.02; N, 2.90%.

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. additionwas added
  4. extractionthe organic material was extracted into dichloromethane (1×100 ml and 3×50 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried overmagnesium sulfate
  7. customevaporated
  8. customThe crude product was purified by column chromatography over silica gel 60
  9. customto afford a yellow solid, which
  10. customwas recrystallised from dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-817c5153c1384d15a08f3025ea462d14
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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