Water → HCID 89771099, compound

HRID 711345Notes

Reaction equation

HRID 711345 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@H:12]([N:14]([CH3:21])[S@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH3:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Zn](CC)[CH2:23][CH3:24].O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:23]([C:2]1[CH:3]=[C:4]([C@H:12]([N:14]([CH3:21])[S@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])[CH3:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[CH3:24]

Participants

6

Reactant 3

HCID 962WaterHCID 118492011HCID 118492011, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 89771099HCID 89771099, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
6 °C

Procedure

A mixture of (S)-N-((R)-1-(3-bromo-5-(trifluoromethyl)phenyl)ethyl)-N,2-dimethyl propane-2-sulfinamide (1 g, 2.6 mmol), Pd(PPh3)2Cl2 (182 mg, 0.26 mmol) and Et2Zn (640 mg, 5.2 mmol) in THF (10 mL) under N2 atmosphere was stirred at 6° C. for 16 h. The reaction was poured into water (15 mL) and then extracted with EtOAc (2×30 mL). The combined organic layers were dried over anhydrous Na2SO4 and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=10/1 to 1/1) to give the title compound (700 mg, yield: 80.3%); m/z (ES+): 336 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (PE/EtOAc=10/1 to 1/1)

Sources & evidence

ORD record
ord-9d07fad3039f4227947647d1279c1147
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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