Cesium carbonate → HCID 59474456, compound

HRID 1507025Notes

Reaction equation

HRID 1507025 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.Br[C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 594746911-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-benzo[D]imidazole

Product 1

HCID 59474456HCID 59474456, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole (6 g, 23.1 mmol) in dioxane/water (50 mL) was added 3-bromophenol (4.8 g, 27.7 mmol), Pd(dppf)Cl2 (0.3 g) and Cs2CO3 (15 g, 46.2 mmol). The reaction mixture was heated at 100° C. for 3 h, cooled and concentrated. The crude reaction mixture was purified by column chromatography. (4.8 g, yield 92%) MS (ESI+) e/z: 225.1.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe crude reaction mixture
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a1a87df517d5451cb30d3d4975e3b9e1
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

Loading…