3-Bromoquinoline → HCID 11401811, compound

HRID 717789Notes

Reaction equation

HRID 717789 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>CN(C=O)C.O.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>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 214133-BromoquinolineHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 11401811HCID 11401811, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

3-Bromo quinoline (2 g, 0.0096 mol) was dissolved in DMF:water (3:1, 20 mL), and potassium phosphate (6 g, 0.0288 mol) and 4-fluorophenyl boronic acid (1.6 g, 0.011 mol) were added at RT. The reaction mixture was degassed for 5 min, and Pd(PPh3)4 (0.55 g, 0.00048 mol) was added. The reaction mixture was heated by microwave at 80° C. for 1 h. After completion of reaction (monitored by TLC), the mixture was diluted with water (150 mL) and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum, the residue was purified by column chromatography (30% EtOAc:Hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a white solid (1.4 g, 66% yield).

Workup

  1. customThe reaction mixture was degassed for 5 min
  2. customAfter completion of reaction (monitored by TLC)
  3. extractionextracted with EtOAc (3×150 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customthe residue was purified by column chromatography (30% EtOAc:Hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-ead1de98cc454ca6b3fa336d277dffca
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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