Sodium Bicarbonate → HCID 23502837, compound

HRID 547750Notes

Reaction equation

HRID 547750 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:27][C:28]([F:46])([F:45])[C:29]1[CH:30]=[C:31]([C:39]([CH3:44])([CH3:43])[C:40](Cl)=[O:41])[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[F:37][C:35]([F:36])([F:38])[C:33]1[CH:32]=[C:31]([C:39]([CH3:44])([CH3:43])[C:40]([N:8]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH3:9])=[O:41])[CH:30]=[C:29]([C:28]([F:27])([F:45])[F:46])[CH:34]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 23502811[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 23502837HCID 23502837, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 20 g (79 mmol) [6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine in 200 ml tetrahydrofuran were added dropwise at 0° C. 113 ml (94.8 mmol) of a 0.91 M solution of potassium bis(trimethylsilyl)amide in tetrahydrofuran. The reaction mixture was stirred at room temperature for 30 min. After cooling to 0° C. 27.7 g (86.9 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride were added dropwise. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction mixture was treated with 220 ml 1 N sodium hydrogencarbonate solution and extracted with three 200-ml portions of ethyl acetate. The combined organic layers were dried over sodium sulfate and triturated with 150 ml diethylether to give 34.6 g (82%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling to 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred at room temperature for 1 h
  4. extractionextracted with three 200-ml portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customtriturated with 150 ml diethylether

Sources & evidence

ORD record
ord-9fc1fd1c07414d68a3a92c418c95a268
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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