4-Chlorophenylboronic acid → 1-[4'-Chloro-4-(pyrrolidine-1-carbonyl)-biphen-2-yl]-ethanone

HRID 1788549Notes

Reaction equation

HRID 1788549 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.CO.C([O-])(O)=O.[Na+].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>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:3]([C:15](=[O:17])[CH3:16])=[CH:4][C:5]([C:8]([N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[O:9])=[CH:6][CH:7]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 689280571-[2-Iodo-5-(pyrrolidine-1-carbonyl)phenyl]ethanone

Product 1

HCID 860272831-[4'-Chloro-4-(pyrrolidine-1-carbonyl)-biphen-2-yl]-ethanoneYield 96%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of Compound 419c (0.29 g, 0.845 mmol), 4-chlorobenzeneboronic acid (0.159 g, 1.02 mmol)) and Pd(PPh3)4 (97 mg) in toluene (25 mL), MeOH (6 mL) and saturated NaHCO3 (2.5 mL) was stirred under Ar at 70° C. for 16 h. After evaporation of solvent, the residue was dissolved in CHCl3 (30 mL) and filtered. The filtrate was evaporated to dryness. The residue was purified by chromatography using CHCl3-MeOH (80:1 to 30:1) as the eluent to give an oil (0.266 g, 96%). MS: 328.08 (M+H+).

Workup

  1. customAfter evaporation of solvent
  2. dissolutionthe residue was dissolved in CHCl3 (30 mL)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-64def31f788d42a4ab02b00dbb8098c9
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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