Water → 2-(6'-(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridin-6-yl)benzo[d]thiazole

HRID 521552Notes

Reaction equation

HRID 521552 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[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.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[S: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

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 667997612-(5-Bromopyridin-2-yl)benzo[d]thiazoleHCID 668014339-(4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenyl)-9H-carbazole

Product 1

HCID 569438302-(6'-(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridin-6-yl)benzo[d]thiazoleYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7 (0.841 g, 1.89 mmol), 9 (0.549 g, 1.89 mmol), tetrakis(triphenylphosphine)palladium(0) (109 mg, 94.2 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 18 h. Upon confirming consumption of the starting materials by TLC (SiO2, CH2Cl2), the mixture was cooled to RT and poured over CHCl3 (300 mL). The organics were then washed with sat. NaHCO3, H2O and brine, dried over MgSO4, filter and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 100% CH2Cl2 to 49:1 CH2Cl2-acetone) provided 19 (0.72 g, 72%) as a light yellow solid.

Workup

  1. customwas degassed with argon for about 20 min
  2. customThe stirring reaction mixture
  3. customconsumption of the starting materials by TLC (SiO2, CH2Cl2)
  4. temperaturethe mixture was cooled to RT
  5. additionpoured over CHCl3 (300 mL)
  6. washThe organics were then washed with sat. NaHCO3, H2O and brine
  7. dry with materialdried over MgSO4
  8. filtrationfilter
  9. concentrationconcentrated in vacuo
  10. customPurification of the crude product via flash chromatography (SiO2, 100% CH2Cl2 to 49:1 CH2Cl2-acetone)

Sources & evidence

ORD record
ord-5d5dca33e82f4d6bb80653b219defe69
Source dataset
uspto-grants-2016_05
Patent number
US09328086B2

Reaction notes

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