Methane → HCID 11833097, compound

HRID 429190Notes

Reaction equation

HRID 429190 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.CO.C(Cl)(Cl)Cl.C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:2]3=[N:3][CH:4]=[CH:5][CH:6]=[C:7]3[NH:8][C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 9237DabcoHCID 21584188Chloroform methanolHCID 73088680HCID 73088680, compound

Product 1

HCID 11833097HCID 11833097, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (2-chloropyridin-3-yl)-[2-(4-fluorophenyl)-1-(pyridin-4-yl)vinyl]amine (6.0 g, 18.5 mmol) and DABCO® (6.2 g, 55 mmol) in dimethylformamide (75 ml) was added bis(triphenylphosphine)palladium(II) chloride (650 mg, 0.926 mmol) and the reaction mixture was heated at 120° C. under an argon atmosphere. After 4 h, dimethylformamide was removed in vacuo and the residue was heated in ethyl acetate/methanol mixture. The product was filtered off to give a green solid which was redissolved in boiling methanol/chloroform mixture and treated with charcoal. The solution was filtered through a pad of Celite and the filtrate was concentrated to give 3-(4-fluorophenyl)-2-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridine as a pale yellow solid (5.27 g).

Workup

  1. customdimethylformamide was removed in vacuo
  2. temperaturethe residue was heated in ethyl acetate/methanol mixture
  3. filtrationThe product was filtered off
  4. customto give a green solid which
  5. dissolutionwas redissolved
  6. filtrationThe solution was filtered through a pad of Celite
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c89c9d3374a4e048f79778f39dcf72e
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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