Pyridine → 2-[(3-Chloro-4-fluorophenyl)(1-phenylethyl)amino]propan-1-ol

HRID 1822178Notes

Reaction equation

HRID 1822178 reaction equation
[C:1]1([CH:7]([NH:9][CH:10]([CH3:13])[CH2:11][OH:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[Cl:30]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Cl:30][C:22]1[CH:23]=[C:24]([N:9]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH:10]([CH3:13])[CH2:11][OH:12])[CH:25]=[CH:26][C:21]=1[F:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 434996922-[(1-Phenylethyl)amino]propan-1-ol

Product 1

HCID 116881202-[(3-Chloro-4-fluorophenyl)(1-phenylethyl)amino]propan-1-ol

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(1-phenylethyl)amino]propan-1-ol (5-5, 0.027 g, 0.151 mmol) in CH2Cl2 (1.0 mL) was treated with Cu(OAc)2 (0.041 g, 0.227 mmol), pyridine (0.024 mL, 0.302 mmol), and 4-fluoro-3-chloro-phenylboronic acid (0.026 g, 0.149 mmol). 4 A MS (20 mg) were added and the resulting solution stirred 24 h. Upon completion, the reaction mixture was filtered and the filtrate was purified by reverse phase liquid chromatography (Semi-prep YMC C-18 Column 5% CH3CN/H2O up to 95% CH3CN/H2O) to give 2-[(3-chloro-4-fluorophenyl)(1-phenylethyl)amino]propan-1-ol (5-6) as a brown oil. MS 308.3 found 308.8 (M+H+) required.

Workup

  1. addition4 A MS (20 mg) were added
  2. filtrationUpon completion, the reaction mixture was filtered
  3. customthe filtrate was purified by reverse phase liquid chromatography (Semi-prep YMC C-18 Column 5% CH3CN/H2O up to 95% CH3CN/H2O)

Sources & evidence

ORD record
ord-7ec9d61050d0421da0e885be2358903a
Source dataset
uspto-grants-2009_10
Patent number
US07608739B2

Reaction notes

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