HCID 117760043, compound → HCID 117760223, compound

HRID 709836Notes

Reaction equation

HRID 709836 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:18][C:19]2([C:24]#[N:25])[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:6]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[F:17])=[N:7][CH:8]=1.[CH:26]1([CH:29]([C:36]2[C:41]([F:42])=[CH:40][N:39]=[C:38]([OH:43])[CH:37]=2)[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:28][CH2:27]1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[C:24]([C:19]1([CH2:18][C:5]2[CH:4]=[C:3]([CH2:2][O:43][C:38]3[CH:37]=[C:36]([CH:29]([CH:26]4[CH2:28][CH2:27]4)[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:41]([F:42])=[CH:40][N:39]=3)[CH:8]=[N:7][C:6]=2[C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[F:17])[CH2:20][CH2:21][CH2:22][CH2:23]1)#[N:25]

Participants

5

Reactant 2

HCID 117760043HCID 117760043, compoundHCID 178471099HCID 178471099, compound

Product 1

HCID 117760223HCID 117760223, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 1-((5-(bromomethyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methyl)cyclopentanecarbonitrile (48 mg) and ethyl 3-cyclopropyl-3-(5-fluoro-2-hydroxypyridin-4-yl)propanoate (40 mg) obtained in Example 42, step E, in toluene (1 mL) was added silver carbonate (48 mg), and the mixture was refluxed for 2 hr. The reaction mixture was filtered, and the solvent in the filtrate was evaporated under reduced pressure and the residue was purified by preparative HPLC (water/acetonitrile, TFA added) to give the title compound (11 mg) as a yellow oil.

Workup

  1. temperaturethe mixture was refluxed for 2 hr
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent in the filtrate was evaporated under reduced pressure
  4. customthe residue was purified by preparative HPLC (water/acetonitrile, TFA added)

Sources & evidence

ORD record
ord-4d935b96aa6347dabb59f51732ea6376
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…