2-Bromopyridine → HCID 68474901, compound

HRID 2089613Notes

Reaction equation

HRID 2089613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH2:11])[CH:10]=1)[NH:7][C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:5]2.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([NH:11][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:10]=1)[NH:7][C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:5]2

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68478397HCID 68478397, compound

Product 1

HCID 68474901HCID 68474901, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

7-Amino-5-chloro-2-phenyl-1H-indole (200 mg, 0.82 mmol) prepared in Example 3 was dissolved in toluene (30 mL). 2-Bromopyridine (182 mg, 1.15 mmol), Pd2(dba)3, Xantphos (42 mg, 0.07 mmol) and Na2CO3 were added thereto. The mixture was degassed, and stirred for 12 h at 100° C. After completion of the reaction, the reaction mixture was filtered through a cellite. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/3) to give the title compound (25 mg, Yield 13%).

Workup

  1. customThe mixture was degassed
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through a cellite
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (eluent: EtOAc/n-Hex=1/3)

Sources & evidence

ORD record
ord-1d7eee86fabd44fc987871be429bb4a2
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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