Water → 2-(6'-(Benzo[d]thiazol-2-yl)-3,3'-bipyridin-6-yl)benzo[d]oxazole

HRID 521551Notes

Reaction equation

HRID 521551 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[CH:27][C:28]([C:31]3[S:32][C:33]4[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=4[N:35]=3)=[N:29][CH:30]=2)O1.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.C1COCC1>[S:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[C:28]1[N:29]=[CH:30][C:25]([C:2]2[CH:7]=[N:6][C:5]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][CH:3]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 469416132-(5-Bromo-2-pyridinyl)benzoxazoleHCID 668063572-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)benzo[d]thiazole

Product 1

HCID 569438292-(6'-(Benzo[d]thiazol-2-yl)-3,3'-bipyridin-6-yl)benzo[d]oxazoleYield 84.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure for 17, 11 (0.558 g, 2.03 mmol), 16 (0.700 g, 2.07 mmol), tetrakis(triphenylphosphine)palladium(0) (117 mg, 102 μmol), Na2CO3 (1.59 g, 15.0 mmol), H2O (15 mL) and THF (25 mL) yielded an insoluble white solid (0.70 g, 84%) after filtration.

Sources & evidence

ORD record
ord-c5ecddb5e7a041a28f85ff72c9cfa504
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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