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

Water → Tert-butyl 4-bromo-3-(bromomethyl)phenyl(5-cyano-6-methoxypyridin-2-yl)carbamate

HRID 1260175
Notes
Print preview

Reaction equation

HRID 1260175 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([O:24][CH3:25])[N:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH3:26].[Br:27]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([O:24][CH3:25])[N:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH2:26][Br:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67306440Tert-butyl 4-bromo-3-methylphenyl(5-cyano-6-methoxypyridin-2-yl)carbamate

Product 1

HCID 67305601Tert-butyl 4-bromo-3-(bromomethyl)phenyl(5-cyano-6-methoxypyridin-2-yl)carbamateYield 162.2%

Reagents, catalysts & solvents 2

HCID 6547
Azobisisobutyronitrile
Catalyst
HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of tert-butyl 4-bromo-3-methylphenyl(5-cyano-6-methoxypyridin-2-yl)carbamate (2.85 g, 6.81 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (0.909 g, 5.11 mmol) and azobisisobutyronitrile (0.042 g, 0.26 mmol). The mixture was refluxed under nitrogen at 95° C. for two hours. The reaction was cooled to room temperature, water was added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give crude tert-butyl 4-bromo-3-(bromomethyl)phenyl(5-cyano-6-methoxypyridin-2-yl)carbamate (4.12 g). The product was used in the next step without further purification.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4defb8e98e2448a68e5882fbe4187745
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08470803B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes