Dichloromethane → HCID 178519542, compound

HRID 2267201Notes

Reaction equation

HRID 2267201 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[O:9])[N:3]=1.[C-:10]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11]1.[CH-:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.[Fe+2:23].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO.O.C1(C)C=CC=CC=1>[C-:10]1([C:2]2[N:3]=[C:4]([CH:8]=[O:9])[CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11]1.[CH-:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.[Fe+2:23]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 1539836212152-94-2

Product 1

HCID 178519542HCID 178519542, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

See Scheme 1. Toluene (500 mL) was added to a mixture of 2-bromo-6-pyridinecarboxaldehyde (16.25 g, 87.36 mmol, purchased from Sigma-Aldrich), ferrocenylboronic acid (24.10 g, 104.9 mmol, purchased from Sigma-Aldrich), and (dppf)PdCl2.CH2Cl2 (2.14 g, 2.62 mmol, purchased from Strem), under a nitrogen atmosphere. Then a nitrogen-sparged solution of Na2CO3 (210 mL, 210 mmol) in 4:1 water:methanol was added. The biphasic mixture was heated to 60° C. After 1 hour, the solution was heated to 80° C. for one week. The mixture was then filtered and the organics were separated and dried over MgSO4. Evaporation yielded the crude 6-ferrocenyl-2-pyridinecarboxaldehyde which was purified on SiO2 using 3:1 to 4:1 CH2Cl2:hexane as the elutant. Yield: 6.02 g, 23.7%. 1H NMR (C6D6): δ 10.18 (1H, s), 7.58 (1H, d), 8.03-6.85 (2H, m), 4.91 (2H, m), 4.20 (2H, m), 3.86 (5H, s).

Workup

  1. temperaturethe solution was heated to 80° C. for one week
  2. filtrationThe mixture was then filtered
  3. customthe organics were separated
  4. dry with materialdried over MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-dcf33cad366d4f36a32a9a67ff87d7a7
Source dataset
uspto-grants-2010_12
Patent number
US07858817B2

Reaction notes

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