Potassium bis(trimethylsilyl)amide → HCID 23502837, compound

HRID 1835335Notes

Reaction equation

HRID 1835335 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](C)(C)[N-][Si](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>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

5

Reactant 3

HCID 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 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 180 mg (0.711 mmol) [6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine in 7 ml dry tetrahydrofuran 0.86 ml of a 0.91 M solution (0.78 mmol) of potassium hexamethyldisilazide in tetrahydrofuran was added at room temperature under an atmosphere of argon. After 45 min 295 mg (0.924 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride were added. The reaction mixture was stirred at room temperature for 3 h. Quenching with water was followed by dilution with tert-butyl methyl ether and washing with 2 M aqueous sodium carbonate solution and brine. The combined aqueous layers were extracted with two portions of tert-butyl methyl ether. The combined organic extracts were dried with sodium sulfate and concentrated. Flash chromatography gave 254 mg (67%) of the title compound as a light yellow solid.

Workup

  1. customQuenching with water
  2. washwashing with 2 M aqueous sodium carbonate solution and brine
  3. extractionThe combined aqueous layers were extracted with two portions of tert-butyl methyl ether
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3e4ded52720c4178872967328eb7935c
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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