1,2-Dimethoxyethane → HCID 18363404, compound

HRID 381508Notes

Reaction equation

HRID 381508 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH:11]=[C:10](I)[CH:9]=[C:8]2[C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Ba+2].[OH-].COCCOC>CCOC(C)=O.O>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:9]=[C:8]2[C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 6093286Barium hydroxideHCID 9928026HCID 9928026, compound

Product 1

HCID 18363404HCID 18363404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a 100 mL round bottomed flask with a stirring bar, reflux condenser and an argon inlet was added 1-[1-(4-fluorobenzyl)-4-iodo-1H-pyrrol-2-yl]ethanone AIII-1-1 (1.00 g, 2.91 mmol), phenylboronic acid (0.431 g, 3.54 mmol), tetrakis(triphenylphosphine)palladiumo (0.20 g, 0.17 mmol), barium hydroxide (1.37 g, 4.37 mmol), DME (40 mL), and H2O (5 mL). This well stirred mixture was heated at reflux 4 h. The reaction mixture was cooled to 20° C. and diluted with EtOAc. This solution was washed with H2O, 1N HCl, H2O, and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an amorphous material. The crude product was chromatographed on silica gel using 15% EtOAc in hexanes as eluant to give 1-[1-(4-fluorobenzyl)-4-phenyl-1H-pyrrol-2-yl]ethanone AIX-1-1 as an oil. 1H NMR (CDCl3) δ 2.47 (3H, s), 5.57 (2H, s), 6.98 (2H, m), 7.13 to 7.28 (5H, complex multiplet), 7.36 (2H, m), 7.51 (2H, m).

Workup

  1. temperatureTo a 100 mL round bottomed flask with a stirring bar, reflux condenser and an argon inlet
  2. temperaturewas heated
  3. temperatureat reflux 4 h
  4. washThis solution was washed with H2O, 1N HCl, H2O, and brine
  5. customDrying
  6. filtration(MgSO4), filtration and removal of the solvent in vacuo
  7. customgave an amorphous material
  8. customThe crude product was chromatographed on silica gel using 15% EtOAc in hexanes as eluant

Sources & evidence

ORD record
ord-4f691b0adcca4a1b81ee2fa1e29b1158
Source dataset
uspto-grants-2001_10
Patent number
US06306891B1

Reaction notes

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