Water → 9-[4-[5-[6-(1-Phenylbenzimidazol-2-yl)-3-pyridinyl]-2-pyridinyl]phenyl]carbazole

HRID 521554Notes

Reaction equation

HRID 521554 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:33]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:27]5[C:22]4=[CH:23][CH:24]=[CH:25][CH:26]=5)=[CH:17][CH:16]=3)=[N:13][CH:14]=2)O1.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:47]1([N:46]2[C:45]3[CH:53]=[CH:54][CH:55]=[CH:56][C:44]=3[N:43]=[C:42]2[C:39]2[N:40]=[CH:41][C:36]([C:9]3[CH:14]=[N:13][C:12]([C:15]4[CH:16]=[CH:17][C:18]([N:21]5[C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=6[C:28]6[C:33]5=[CH:32][CH:31]=[CH:30][CH:29]=6)=[CH:19][CH:20]=4)=[CH:11][CH:10]=3)=[CH:37][CH:38]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 668014339-(4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenyl)-9H-carbazoleHCID 668063662-(5-bromopyridin-2-yl)-1-phenyl-1H-benzo[d]imidazole

Product 1

HCID 569439279-[4-[5-[6-(1-Phenylbenzimidazol-2-yl)-3-pyridinyl]-2-pyridinyl]phenyl]carbazoleYield 70%

Reagents, catalysts & solvents 4

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

Procedure

Following the procedure for 19, 7 (0.757 g, 1.70 mmol), 13 (0.594 g, 1.70 mmol), tetrakis(triphenylphosphine)palladium(0) (98 mg, 85 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded 21 (0.70 g, 70% yield) as a light yellow solid after flash chromatography (SiO2, 100% CH2Cl2 to 19:1 CH2Cl2-acetone).

Sources & evidence

ORD record
ord-94be7fe26e32435a8e2ecfa02342e535
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

Loading…