Water → HCID 59200987, compound

HRID 1690160Notes

Reaction equation

HRID 1690160 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:24][CH2:25][O:26][CH3:27])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[CH2:28][CH2:29][CH3:30])[CH:7]=1.O.[CH3:32][N:33](C)C=O>[C-]#N.[Zn+2].[C-]#N>[F:19][C:16]([F:17])([F:18])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[N:4][CH:3]=[C:2]([CH:7]=2)[C:32]#[N:33])=[C:10]([CH2:28][CH2:29][CH3:30])[CH:11]=1)([O:24][CH2:25][O:26][CH3:27])[C:20]([F:21])([F:22])[F:23]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 59200929HCID 59200929, compound

Product 1

HCID 59200987HCID 59200987, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

To a solution of 3-bromo-5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy) pyridine (320 mg, 637 μmol) in N,N-dimethylformamide (5 mL), zinc cyanide (112 mg) and tetrakis triphenylphosphine palladium complex (74 mg) were added at room temperature under an argon atmosphere, and the resultant mixture was allowed to react in a microwave (80 watts, 10 minutes). After completion of the reaction, the reaction solution was added with water at room temperature, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (239 mg, yield 84%) was obtained as a colorless oil.

Workup

  1. customto react in a microwave (80 watts, 10 minutes)
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-432328a988674530a273826ef99269f3
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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