Water → 4-(6'-(benzo[d]thiazol-2-yl)-3,3'-bipyridin-6-yl)-N,N-diphenylaniline

HRID 521546Notes

Reaction equation

HRID 521546 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[S: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.CO.C(Cl)Cl.C1COCC1>[S: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 667997612-(5-Bromopyridin-2-yl)benzo[d]thiazoleHCID 66801665N,N-diphenyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)aniline

Product 1

HCID 569437324-(6'-(benzo[d]thiazol-2-yl)-3,3'-bipyridin-6-yl)-N,N-diphenylanilineYield 81%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Following the procedure for 3, 2 (0.521 g, 1.16 mmol), 9 (0.338 g, 1.16 mmol), tetrakis(triphenylphosphine)palladium(0) (67.1 mg, 58.1 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded 10 (0.50 g, 81% yield) as a bright yellow solid after flash chromatography (SiO2, 100% CH2Cl2 to 99:1 CH2Cl2—CH3OH).

Sources & evidence

ORD record
ord-94f025b8d0034f5da46fe3601cf1e3f1
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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