(Diethylamino)sulfur trifluoride → HCID 59726028, compound

HRID 422576Notes

Reaction equation

HRID 422576 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12](O)([CH3:14])[CH3:13])=[N:7][N:6]=[CH:5]2.CCN(S(F)(F)[F:22])CC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([F:22])([CH3:14])[CH3:13])=[N:7][N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59726021HCID 59726021, compound

Product 1

HCID 59726028HCID 59726028, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(6-chlorophthalazin-1-yl)propan-2-ol (154 mg, 0.69 mmol) in 5 mL of DCM at −78° C. was treated with DAST (0.11 mL, 0.76 mmol) slowly. It was warmed slowly to room temperature overnight, then quenched with saturated NaHCO3 solution and extracted with CH2Cl2. The DCM layer was dried over MgSO4, filtered and concentrated. Purification on an ISCO (12 g column, 10-35% EtOAc:Hexanes) afforded 6-chloro-1-(2-fluoropropan-2-yl)phthalazine (84 mg, 54% yield) as a pale yellow, viscous oil. MS (ESI, pos. ion) m/z: 225.1 (M+1).

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionextracted with CH2Cl2
  3. dry with materialThe DCM layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on an ISCO (12 g column, 10-35% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-42cb9035a4da40d7b2d16a315cdff015
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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