(4-Methoxyphenyl)boronic acid → HCID 131733102, compound

HRID 1520262Notes

Reaction equation

HRID 1520262 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]2[CH:34]=[CH:33][C:19]([C:20]([N:22]3[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23]3)=[O:21])=[CH:18][CH:17]=2)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:35])[CH:3]=1.[F-].[K+].[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCCC1>[F:12][C:11]([F:14])([F:13])[CH2:10][CH2:9][CH:8]([NH:15][C:16]1[CH:34]=[CH:33][C:19]([C:20]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23]2)=[O:21])=[CH:18][CH:17]=1)[C:5]1[CH:6]=[CH:7][C:2]([C:43]2[CH:44]=[CH:45][C:40]([O:39][CH3:38])=[CH:41][CH:42]=2)=[CH:3][C:4]=1[CH3:35]

Participants

8

Reactant 4

HCID 201262(4-Methoxyphenyl)boronic acidHCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 131733103HCID 131733103, compound

Product 1

HCID 131733102HCID 131733102, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of ethyl (3R)-1-(4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylate (200 mg), palladium acetate (4.0 mg), potassium fluoride (62.8 mg), 4-methoxyphenylboronic acid (109 mg), 2-(di-tert-butylphosphino)biphenyl (10.7 mg) and tetrahydrofuran (2 mL) was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.173 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a1b280f18d3348b48b7e51313696bade
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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