Water → N,N-diphenyl-4-[5-[6-(1-phenylbenzimidazol-2-yl)-3-pyridinyl]-2-pyridinyl]aniline

HRID 521549Notes

Reaction equation

HRID 521549 reaction equation
[C:1]1([N:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:8]2[CH:13]=[CH:12]C(C3C=CC(B4OC(C)(C)C(C)(C)O4)=CN=3)=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:36]1[CH:37]=[CH:38][C:39]([C:42]2[N:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:45]3[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=3[N:43]=2)=[N:40][CH:41]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.CC(C)=O.C(Cl)Cl.C1COCC1>[C:8]1([N:7]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:1]2[CH:6]=[CH:5][C:4]([C:39]3[N:40]=[CH:41][C:36]([C:36]4[CH:41]=[N:40][C:39]([C:42]5[N:46]([C:47]6[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=6)[C:45]6[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=6[N:43]=5)=[CH:38][CH:37]=4)=[CH:37][CH:38]=3)=[CH:3][CH:2]=2)[CH:13]=[CH:12][CH:56]=[CH:44][CH:45]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66801665N,N-diphenyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)anilineHCID 668063662-(5-bromopyridin-2-yl)-1-phenyl-1H-benzo[d]imidazole

Product 1

HCID 56943826N,N-diphenyl-4-[5-[6-(1-phenylbenzimidazol-2-yl)-3-pyridinyl]-2-pyridinyl]anilineYield 176%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

Following the procedure for 3, 2 (0.758 g, 1.69 mmol), 13 (0.592 g, 1.69 mmol), tetrakis(triphenylphosphine)palladium(0) (97.6 mg, 84.5 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded 14 (0.88 g, 88%) as a yellow solid after flash chromatography (SiO2, 100% CH2Cl2 to 9:1 CH2Cl2-acetone).

Sources & evidence

ORD record
ord-e8772d1bd8d2470aa75d6ffd6d451e4f
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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