Toluene → 4,7-di(benzofuran-2-yl)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

HRID 1050684Notes

Reaction equation

HRID 1050684 reaction equation
Br[C:2]1[C:10]2[C:6](=[N:7][N:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH:20]=[C:19]1B(O)O.[C:30](=[O:33])([O-])[O-].[Na+].[Na+].[C:36]1([CH3:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.C(O)CCC.ClCCl.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>[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH:20]=[C:19]1[C:2]1[C:10]2[C:6](=[N:7][N:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:9]=2)[C:5]([C:42]2[O:33][C:30]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH:36]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 866799014,7-dibromo-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

Product 1

HCID 866799074,7-di(benzofuran-2-yl)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 2631-ButanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Intermediate A (1.41 g, 4 mmol), benzofuran-2-ylboronic acid (1.60 g, 9.8 mmol), tetrakis(triphenylphosphine)palladium (0) (0.50 g, 0.43 mmol), sodium carbonate (2.12 g, 20 mmol) in water (10 mL), n-butanol (25 mL), and toluene (25 mL) is heated under argon at 110° C. for 3 days. The reaction mixture is poured into water (200 mL), diluted with dichloromethane (100 mL), and stirred for 1 hour. The solid is filtered off, washed with water (50 mL) followed by dichloromethane (20 mL) and dried to give 4,7-di(benzofuran-2-yl)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole (Example 3), yellow crystals, 745 mg (43%). 1H NMR (400 MHz, CDCl3): δ 8.92 (m, 2H, pyridine), 8.47 (m, 2H, pyridine), 8.16 (s, 2H, benzotriazole), 8.01 (s, 2H, benzofuran), 7.74 (d, J=7.4 Hz, 2H, benzofuran), 7.59 (d, J=7.4 Hz, 2H, benzofuran), 7.37 (td, J=7.7 and 1.1 Hz, 2H, benzofuran), 7.30 (td, J=7.5 and 1.1 Hz, 2H, benzofuran). UV-vis spectrum (dichloromethane): λmax=436 nm. Fluorimetry (dichloromethane): λmax=481 nm.

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with water (50 mL)
  3. customdried

Sources & evidence

ORD record
ord-149d304ae6a1415e9514783bb1ea99a3
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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