Pyridine → HCID 66818961, compound

HRID 1024819Notes

Reaction equation

HRID 1024819 reaction equation
[CH:1]([O:4][C:5](=[O:32])[NH:6][CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:31])[C:15]2[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:16]=2)[CH2:9][CH2:8]1)([CH3:3])[CH3:2].[Br:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1.N1C=CC=C[CH:44]=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:4][C:5](=[O:32])[NH:6][CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:31])[C:15]2[CH:16]=[C:17]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:18]=[C:19]([O:21][C:38]3[CH:37]=[CH:36][CH:35]=[C:34]([Br:33])[CH:39]=3)[CH:20]=2)[CH2:9][CH2:8]1)([CH3:44])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2734318(3-Bromophenyl)boronic acidHCID 66818508HCID 66818508, compound

Product 1

HCID 66818961HCID 66818961, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

{4-[3-(4-Cyano-phenoxy)-5-hydroxy-benzoylamino]-cyclohexyl}-carbamic acid isopropyl ester (1.0 g, 2.2 mmol) and copper acetate (0.4 g, 2.2 mmol), dissolved in 30 ml of dichloromethane, were charged in a 100 ml capacity seal-tube. 3-bromophenyl boronic acid (0.667 g, 3.32 mmol), 4 Å molecular sieves (3.0 g) and 0.438 g (5.53 mmol) of pyridine, in 20 ml of dichloromethane, was added to the reaction mixture in a sealed-tube and reaction mixture was stirred at RT for 20 h. After reaction completion 2.0 g of silica-gel was added and the mixture was filtered. Thus obtained filterate was concentrated under reduced pressure and subjected to column chromatography to afford 0.3 g of the required product. Percentage purity (LCMS): 86.0%, (M+1)=605.1+1.

Workup

  1. additionwere charged in a 100 ml capacity seal-tube
  2. customreaction mixture
  3. customAfter reaction completion 2.0 g of silica-gel
  4. additionwas added
  5. filtrationthe mixture was filtered
  6. concentrationThus obtained filterate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d22e647d05674e09b8317f60370a5069
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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