Water → 2-[5-[6-(4-Carbazol-9-ylphenyl)-3-pyridinyl]-2-pyridinyl]-1,3-benzoxazole

HRID 521553Notes

Reaction equation

HRID 521553 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[O:43][C:44]3[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=3[N:46]=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>[CH:23]1[C:22]2[N:21]([C:18]3[CH:19]=[CH:20][C:15]([C:12]4[N:13]=[CH:14][C:9]([C:36]5[CH:41]=[N:40][C:39]([C:42]6[O:43][C:44]7[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=7[N:46]=6)=[CH:38][CH:37]=5)=[CH:10][CH:11]=4)=[CH:16][CH:17]=3)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 469416132-(5-Bromo-2-pyridinyl)benzoxazoleHCID 668014339-(4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenyl)-9H-carbazole

Product 1

HCID 569439262-[5-[6-(4-Carbazol-9-ylphenyl)-3-pyridinyl]-2-pyridinyl]-1,3-benzoxazoleYield 81%

Reagents, catalysts & solvents 4

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

Procedure

Following the procedure for 19, 7 (0.868 g, 1.95 mmol), 11 (0.535 g, 1.95 mmol), tetrakis(triphenylphosphine)palladium(0) (112 mg, 97.2 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded 20 (0.81 g, 81%) as a white solid after flash chromatography (SiO2, 100% CH2Cl2 to 19:1 CH2Cl2-acetone).

Sources & evidence

ORD record
ord-6fd0d2cba0594291b722516d8d9ba6c8
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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