Ammonium Chloride → HCID 58443408, compound

HRID 2067954Notes

Reaction equation

HRID 2067954 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.C([Li])CCC.[CH:17](=[N:21][S@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[CH2:18][CH2:19][CH3:20].[Cl-].[NH4+]>C(OCC)C>[F:9][C:8]([F:11])([F:10])[C:4]1[N:3]=[C:2]([C@@H:17]([NH:21][S@:22]([C:24]([CH3:25])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:19][CH3:20])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 27829022-Bromo-6-(trifluoromethyl)pyridineHCID 86657764HCID 86657764, compoundHCID 178418339Butyllithium

Product 1

HCID 58443408HCID 58443408, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-bromo-6-trifluoromethyl-pyridine (480 mg, 2.2 mmol) in anhydrous diethyl ether (20 mL) at −78° C. is added n-butyllithium (1.6 M in hexanes, 1.5 mL, 2.4 mmol) dropwise over 20 min. After stirring at −78° C. for 30 min, (S)-2-methyl-propane-2-sulfinic acid butylideneamide is added. The resultant mixture is stirred at −78° C. for 30 min and is then allowed to warm gradually to room temperature overnight. The reaction mixture is poured into saturated aqueous ammonium chloride solution (30 mL) and extracted with EtOAc (3×30 mL). The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo to afford (S,S)-2-methyl-propane-2-sulfinic acid 1-(6-trifluoromethyl-pyridin-2-yl)-butylamide as a yellow oil (290 mg, 42%).

Workup

  1. temperatureto warm gradually to room temperature overnight
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aab12a71d6e94f60987a98560aa707a5
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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