Water → N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)pivalamide

HRID 63785Notes

Reaction equation

HRID 63785 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([Br:19])=[CH:11][N:10]=1.C(N(CC)CC)C.O>ClCCl>[Br:19][C:12]1[C:13]([C:15]([F:18])([F:16])[F:17])=[CH:14][C:9]([NH:8][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 288753485-Bromo-4-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 97301693N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)pivalamideYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an ice bath, 29.8 g of pivaloyl chloride (226 mmol) was added dropwise to a solution of compound 5 (50.0 g, 207 mmol) and triethylamine (37.9 mL) in dichloromethane (300.0 mL) within one hour and then stirred for 2 hours until the starting materials disappeared. 150 mL of water was added into the reaction solution and stirred at room temperature for 10 minutes. The organic layer was separated, dried over anhydrous sodium sulfate, concentrated, and separated through a short column with ethyl acetate to give white solid (57.7 g, 85.6%).

Workup

  1. stirringstirred at room temperature for 10 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customseparated through a short column with ethyl acetate

Sources & evidence

ORD record
ord-0f6fd8b006f14602ba848464c8fc3fcd
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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