Tetrahydrofuran → HCID 67171101, compound

HRID 877378Notes

Reaction equation

HRID 877378 reaction equation
[CH3:1][C:2]([S:5](/[N:7]=[CH:8]/[C:9]1[N:10]=[N:11][N:12]([CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:13]=1)=[O:6])([CH3:4])[CH3:3].[F:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[CH:24][C:25]=1[F:26].C1COCC1>C(Cl)Cl>[F:19][C:20]1[CH:21]=[C:22]([CH:8]([C:9]2[N:10]=[N:11][N:12]([CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:13]=2)[NH:7][S:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 88851176HCID 88851176, compoundHCID 178505835HCID 178505835, compound

Product 1

HCID 67171101HCID 67171101, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a 25 ml round bottom flask containing −78° C. solution of 2-methyl-N-((1E)-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methylene)propane-2-sulfinamide (0.286 g, 0.998 mmol) in 4.0 ml of CH2Cl2 was added dropwise 0.5N 3,4-difluorophenylmagnesium bromide in THF (4.990 ml, 1.495 mmol). The resulting solution was stirred at −78° C. for 30 min, then −20° C. for 16 hours. The reaction mixture was quenched with saturated NH4Cl and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum to give the crude title compound as a light yellow liquid (0.498 g, 93% crude). ES-MS [M+1]+: 401.1. This intermediate was carried over to the next step without further purifications and characterizations.

Workup

  1. wait−20° C. for 16 hours
  2. customThe reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-20ac8b312e354407a4c1880a5882aef8
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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