Water → 6,6'-Di(benzo[d]thiazol-2-yl)-3,3'-bipyridine

HRID 521550Notes

Reaction equation

HRID 521550 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S: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:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[N:6]=[CH:7][C:2]([C:25]2[CH:30]=[N:29][C:28]([C:31]3[S:32][C:33]4[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=4[N:35]=3)=[CH:27][CH:26]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 667997612-(5-Bromopyridin-2-yl)benzo[d]thiazoleHCID 668063572-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)benzo[d]thiazole

Product 1

HCID 569438286,6'-Di(benzo[d]thiazol-2-yl)-3,3'-bipyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9 (0.591 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) was degassed with argon for about 20 min while stirring. The stirring reaction mixture was then maintained under argon at about 80° C. for about 19 h. Upon completion, the mixture was cooled to RT, filtered and the precipitate collected as a white solid (0.83 g, 97%). This compound was found to be insoluble in numerous common organic solvents.

Workup

  1. customwas degassed with argon for about 20 min
  2. customThe stirring reaction mixture
  3. temperatureUpon completion, the mixture was cooled to RT
  4. filtrationfiltered
  5. customthe precipitate collected as a white solid (0.83 g, 97%)

Sources & evidence

ORD record
ord-ea8654c40532450d9b06fb7680ca74bb
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

Loading…