HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Cesium fluoride → Tert-butyl 4-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazine-1-carboxylate

HRID 2172858
Notes
Print preview

Reaction equation

HRID 2172858 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=2)[C:5]([Cl:16])=[CH:4][N:3]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[F-].[Cs+]>CS(C)=O.CCOC(C)=O>[Cl:16][C:5]1[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=2)=[CH:7][C:2]([N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 866919052',5'-Dichloro-3,5-dimethyl-2,4'-bipyridine

Product 1

HCID 67508218Tert-butyl 4-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazine-1-carboxylateYield 78.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl Sulfoxide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2′,5′-dichloro-3,5-dimethyl-2,4′-bipyridine (4.5 g, 17.8 mmol) and tert-butyl piperazine-1-carboxylate (4.0 g, 21.4 mmol) in DMSO (80 mL) was added CsF (5.4 g, 35.6 mmol). Then the mixture was heated at 120° C. for 18 hours. TLC (petroleum ether/EtOAc=2:1) showed that the reaction was complete. It was diluted with EtOAc (200 mL), washed with H2O (70 mL) and brine (70 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether/EtOAc=3:1) to afford title compound (5.6 g, 78%) as white solid.

Workup

  1. washwashed with H2O (70 mL) and brine (70 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (petroleum ether/EtOAc=3:1)

Sources & evidence

ORD record
ord-bd458a8c2dca4990b9939359ea3404ee
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056865B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes