Hydrochloric Acid → HCID 69312695, compound

HRID 2222271Notes

Reaction equation

HRID 2222271 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[CH:2]1.[Cl:12][C:13]1[CH:18]=[C:17](I)[CH:16]=[C:15]([Cl:20])[CH:14]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O1CCOCC1.C1COCC1.C(OCC)C.[Cu]I>[ClH:12].[Cl:12][C:13]1[CH:18]=[C:17]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)=[CH:2]2)[CH:16]=[C:15]([Cl:20])[CH:14]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 764241,3-Dichloro-5-iodobenzeneHCID 8203972-(1H-pyrrol-3-yl)Pyridine

Product 1

HCID 69312695HCID 69312695, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-(1H-pyrrol-3-yl)pyridine (0.072 g, 0.5 mmol), 1,3-dichloro-5-iodobenzene (0.163 g, 0.6 mmol), 1,10-phenanthroline (0.360 g, 2 mmol) and potassium phosphate (0.223 g, 1.05 mmol) in dioxane were degassed for 10 min, then copper (I) iodide (0.038 g, 0.2 mmol) was added and the mixture degassed a further 10 min. The mixture was heated to 110° C. for 4 h. The reaction mixture was quenched with brine, extracted with EtOAc (3×25 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and the residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4) to afford a white solid. The crude material was dissolved in THF (5 mL), 1.2 eq. of 1M HCl in diethyl ether was added and the resulting precipitate was filtered to obtain 2-[1-(3,5-dichlorophenyl)-1H-pyrrol-3-yl]pyridine hydrochloride as a white solid. 1H-NMR (CD3OD, 300 MHz) δ 8.60 (d, 1H), 8.50 (dd, 1H), 8.41 (dd, 1H), 8.34 (d, 1H), 7.80-7.69 (m, 3H), 7.59 (dd, 1H), 7.50-7.49 (m, 1H), 7.11-7.09 (dd, 1H). MS (ESI) 289.0 (M++H).

Workup

  1. customthe mixture degassed a further 10 min
  2. customThe reaction mixture was quenched with brine
  3. extractionextracted with EtOAc (3×25 mL)
  4. washthe combined organic extracts washed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customthe residue was chromatographed on silica gel eluting with EtOAc:hexane (1:4)
  8. customto afford a white solid
  9. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-049375dc3d1445778a33cc937a371924
Source dataset
uspto-grants-2008_05
Patent number
US07371767B2

Reaction notes

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