Tetrahydrofuran → HCID 18187614, compound

HRID 1068196Notes

Reaction equation

HRID 1068196 reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:11]=[N:12][CH:13]=[C:14]([Br:16])[CH:15]=1.[Cl-].[NH4+].[CH2:19]1COCC1>[Cl-].[Zn+2].[Cl-].[Cu](I)I.[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:16][C:14]1[CH:13]=[N:12][CH:11]=[C:10]([CH2:19][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 693693,5-DibromopyridineHCID 178478979HCID 178478979, compound

Product 1

HCID 18187614HCID 18187614, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 3007855ZincchlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

A dry flask under nitrogen was charged with zinc chloride (16 mL, 0.5M in THF, 8 mmol), and a solution of phenylmagnesium chloride (4 mL, 2.0M in THF, 8 mmol). The mixture was heated to 50 C for 3 h then cooled to room temperature and transferred via cannula to a solution of 3,5-dibromopyridine (1.26 grams, 5.3 mmol), copper iodide (61 mg, 0.32 mmol), and bis(diphenylphosphino)ferrocene palladium dichloride (218 mg, 0.27 mmol) in 15 mL THF. The resulting mixture was heated to 50 C overnight. Sat'd ammonium chloride was added and the mixture was extracted with EtOAc. The organic portion was dried over sodium sulfate and concentrated. Flash chromatography (8/1 hexane/EtOAc) afforded 433 mg (33%) of the title compound. 1H NMR (400 MHz, CDCl3). δ4.02 (s, 2H), 7.18-7.4 (m, 8H), 7.65 (s, 1H).

Workup

  1. temperatureThe mixture was heated to 50 C for 3 h
  2. temperatureThe resulting mixture was heated to 50 C overnight
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic portion was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40babad063dc445b91747f54ab39598e
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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