Water → 4-[5-[6-(1,3-benzoxazol-2-yl)-3-pyridinyl]-2-pyridinyl]-N,N-diphenylaniline

HRID 521548Notes

Reaction equation

HRID 521548 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:11]([C:14]3[CH:19]=[CH:18][C:17](B4OC(C)(C)C(C)(C)O4)=[CH:16][N:15]=3)=[CH:10][CH:9]=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[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>[O:43]1[C:44]2[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=2[N:46]=[C:42]1[C:39]1[N:40]=[CH:41][C:36]([C:17]2[CH:16]=[N:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([N:7]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:9][CH:10]=3)=[CH:19][CH:18]=2)=[CH:37][CH:38]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 469416132-(5-Bromo-2-pyridinyl)benzoxazoleHCID 66801665N,N-diphenyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)aniline

Product 1

HCID 569437314-[5-[6-(1,3-benzoxazol-2-yl)-3-pyridinyl]-2-pyridinyl]-N,N-diphenylanilineYield 77%

Reagents, catalysts & solvents 4

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

Procedure

Following the procedure for 3, 2 (0.868 g, 1.94 mmol), 11 (0.533 g, 1.94 mmol), tetrakis(triphenylphosphine)palladium(0) (112 mg, 96.8 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded 12 (0.77 g, 77% yield) as a bright yellow solid after flash chromatography (SiO2, 100% CH2Cl2 to 19:1 CH2Cl2-acetone).

Sources & evidence

ORD record
ord-6e64400b2c7a4e9a8789b9e79cfcee25
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

Loading…