Pyridine → HCID 66615793, compound

HRID 1404253Notes

Reaction equation

HRID 1404253 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([F:25])[CH:31]=4)=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 66615773Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

Product 1

HCID 66615793HCID 66615793, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[4-(5-amino-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.10 g, 0.3 mmol, 1.0 equiv) and 3-fluorophenyl boronic acid (0.086 g, 0.61 mmol, 2.0 equiv) in 5 Ml dichloromethane was added pyridine (0.05 Ml, 0.61 mmol, 2.0 equiv), copper (II) acetate (0.084 g, 0.46 mmol, 1.5 equiv) and 4 Å molecular sieves. The heterogeneous mixture was allowed to stir open to atmosphere for 18 h. Purification by silica gel chromatography (20-45% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.27 (m, 2 H) 1.47 (br. S., 1 H) 1.53 (dd, J=12.51, 2.65 Hz, 1 H) 1.67 (br. S., 1 H) 1.85 (d, J=12.38 Hz, 4 H) 2.29 (d, J=6.57 Hz, 2 H) 3.34 (s, 2 H) 3.64 (s, 3 H) 6.69 (td, J=8.46, 2.53 Hz, 1 H) 6.89 (dt, J=11.62, 2.15 Hz, 1 H) 6.96 (dd, J=7.83, 1.77 Hz, 1 H) 7.33 (d, J=8.34 Hz, 2H) 7.63 (dd, J=8.59, 2.78 Hz, 1 H) 7.84 (d, J=8.59 Hz, 1 H) 7.95 (d, J=8.34 Hz, 2 H) 8.47 (s, 1 H) 8.71 (s, 1H); (M+H)+ 419.3.

Workup

  1. customPurification by silica gel chromatography (20-45% EtOAc in hexanes)

Sources & evidence

ORD record
ord-220194aee7694ccab839a9450019a4e8
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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