Water → HCID 19697339, compound

HRID 862380Notes

Reaction equation

HRID 862380 reaction equation
[Br:1][CH:2]1[CH:10](O)[CH2:9][C:8]2[C:7](=[O:12])[N:6]([C:13]3[CH:18]=[C:17]([O:19][CH2:20][C:21]#[CH:22])[C:16]([Cl:23])=[CH:15][C:14]=3[F:24])[C:5](=[O:25])[C:4]=2[CH2:3]1.CCN(S(F)(F)[F:32])CC.O>ClCCl>[Br:1][CH:2]1[CH:10]([F:32])[CH2:9][C:8]2[C:7](=[O:12])[N:6]([C:13]3[CH:18]=[C:17]([O:19][CH2:20][C:21]#[CH:22])[C:16]([Cl:23])=[CH:15][C:14]=3[F:24])[C:5](=[O:25])[C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 19697338HCID 19697338, compound

Product 1

HCID 19697339HCID 19697339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 995 mg (2.32 mmol) of 5-bromo-2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-6-hydroxy-1H-isoindole-1,3(2H)-dione in 15 mL of dichloromethane was added 430 μL of DAST at 0° C. The mixture was stirred at the same temperature for 1 h. The reaction mixture was then poured into 50 mL of cold water. The aqueous layer was extracted with three 50 mL portions of ethyl acetate. The organic layers were dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and n-hexane to give 626 mg of the title product of Example 4, a compound of the invention, as a whim solid melting at 135°-136.5° C.

Workup

  1. extractionThe aqueous layer was extracted with three 50 mL portions of ethyl acetate
  2. dry with materialThe organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography over silica gel eluting with a 1:4 v
  5. additionv mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-c5954e7d985947e5b4303b6720aa5c0a
Source dataset
uspto-grants-1998_02
Patent number
US05719104

Reaction notes

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