(Diethylamino)sulfur trifluoride → HCID 67003540, compound

HRID 2362721Notes

Reaction equation

HRID 2362721 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3(O)[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([I:11])[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.C(N(S(F)(F)[F:38])CC)C>ClCCl.O1CCOCC1>[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([F:38])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([I:11])[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67003374HCID 67003374, compound

Product 1

HCID 67003540HCID 67003540, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 1-(5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 8A) (330 mg, 0.563 mmol) in dichloromethane (6 mL) and dioxane (6 mL) was added diethylaminosulfur trifluoride (0.149 mL, 1.127 mmol) in a single portion via syringe. The reaction was stirred at 0° C. for 2 hours and was then quenched by the addition of saturated sodium bicarbonate solution and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of hexane to 25% ethyl acetate in hexane, to give the title compound. 1H NMR (300 MHz, DMSO-d6) 8.51 (s, 1H), 8.24 (d, J=2.8 Hz, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 7.24 (s, 1H), 2.80-2.63 (m, 4H), 2.37 (s, 3H), 2.09-1.96 (m, 1H), 1.94-1.85 (m, 1H).

Workup

  1. customwas then quenched by the addition of saturated sodium bicarbonate solution and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  4. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with a gradient of hexane to 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3d40c89f03684e38b5d1625e202a851d
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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