Toluene → n-((1r)-1-Phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamide

HRID 460160Notes

Reaction equation

HRID 460160 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14](Br)[CH:13]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C1(C)C=CC=CC=1>C([O-])([O-])=O.[Na+].[Na+].CCOC(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>[C:1]1([C@H:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:25]3[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[CH:13]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 1140TolueneHCID 201262(4-Methoxyphenyl)boronic acidHCID 681076n-((1r)-1-Phenylethyl)(3-bromo-4-methylphenyl)carboxamide

Product 1

HCID 20803221n-((1r)-1-Phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamideYield 92%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a mixture of N-((1R)-1-phenylethyl)(3-bromo-4-methylphenyl)carboxamide (1.38 g, 4.32 mmol) and 4-methoxyphenylboronic acid (0.53 g, 4.32 mmol) in 10 mL of 2M Na2CO3 aq. soln and 20 mL of toluene was bubbled through N2 for 5 min. Catalyst Pd(PPh3)4 (0.36 g, 0.314 mmol) was then added and the mixture was heated to 80 C for 19 hours under N2. The reaction mixture was cooled to RT and was diluted with 100 mL of EtOAc and 50 mL of water. The organic layer was separated and washed with 50 mL of brine, and dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (CHCl3 to EtOAc) to provide yellow solid (1.0 g, 2.9 mmol, 92%).

Workup

  1. customwas bubbled through N2 for 5 min
  2. temperaturethe mixture was heated to 80 C for 19 hours under N2
  3. customThe organic layer was separated
  4. washwashed with 50 mL of brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (CHCl3 to EtOAc)

Sources & evidence

ORD record
ord-70f5b263d1db490fa4c1bc7f4851d52f
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

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