Pyridine → (S)-2-(1,5-bis(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalate

HRID 931800Notes

Reaction equation

HRID 931800 reaction equation
[C:1]([O:7][CH2:8][C@@H:9]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:10]1[C:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[NH:16][C:15](=[O:21])[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:7][CH2:8][C@H:9]([C:10]1[C:11]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]([C:38]1[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=1)[C:15](=[O:21])[CH:14]=[CH:13]2)[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 742994-Chlorophenylboronic acidHCID 66631890HCID 66631890, compound

Product 1

HCID 66633599(S)-2-(1,5-bis(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalateYield 86.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)ethyl pivalate (8J) (23 mg, 0.05 mmol) and 4-chlorophenylboronic acid (16 mg, 0.10 mmol) in dichloromethane (2 mL) was added copper (II) acetate (9 mg), followed by molecular sieve 4 Å and pyridine (82 μL). The mixture was stirred for 5 days, and filtered and washed with ethyl acetate. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave (S)-2-(1,5-bis(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyethyl pivalate (25 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C33H36Cl2NO4: 580.2. Found: 580.0.

Workup

  1. filtrationfiltered
  2. washwashed with ethyl acetate
  3. concentrationConcentration and purification by flash column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-1e70e60830094af3b72722fec5b16fb4
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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