1,10-Phenanthroline → HCID 22137973, compound

HRID 1827415Notes

Reaction equation

HRID 1827415 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]1[CH3:15].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:22][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([F:16])=[CH:18][CH:19]=2)[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]1[CH3:15]

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 680224-Fluorobenzylic alcoholHCID 153546301-(2-Fluoro-4-iodophenyl)-2,5-dimethyl-1H-pyrrole

Product 1

HCID 22137973HCID 22137973, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(2-fluoro-4-iodo-phenyl)-2,5-dimethyl-1H-pyrrole (33.18 g, 105 mmol), 4-fluorobenzylalcohol (26.6 g, 211 mmol), cesium carbonate (68.6 g, 211 mmol), cuprous iodide (2.0 g, 11 mmol) and 1,10-phenanthroline (3.8 g, 21 mmol) in toluene (52 mL) was heated at 100° C. in an autoclave for 48 h. After cooling to room temperature, the mixture was filtered and poured into sodium hydroxide (1N). The resulting mixture was extracted with toluene and the organic extracts washed with brine, dried and evaporated. The residue was triturated with boiling hexane to leave the title compound (24.7 g, 75%) as a light brown solid. MS: m/e=314.1 (M++H).

Workup

  1. filtrationthe mixture was filtered
  2. additionpoured into sodium hydroxide (1N)
  3. extractionThe resulting mixture was extracted with toluene
  4. washthe organic extracts washed with brine
  5. customdried
  6. customevaporated
  7. customThe residue was triturated with boiling hexane

Sources & evidence

ORD record
ord-ef906712429d47229a39ee28fda5f928
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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