(Diethylamino)sulfur trifluoride → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

HRID 404271Notes

Reaction equation

HRID 404271 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17](O)[CH2:18][N:19]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)[S:20]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.C(N(S(F)(F)[F:47])CC)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]([F:47])[CH2:18][N:19]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)[S:20]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3

Participants

3

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58065820N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

Product 1

HCID 58065896N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

Conditions

Temperature
-78 °C

Procedure

An oven dried 20 ml scintillation vial containing N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (18.3 mg, 0.027 mmol; see representative procedure 3 above) was purged with N2 and charged with anhydrous dichloromethane (1.5 ml, 0.018 M). The sealed vial was cooled in a dry ice acetone bath before the dropwise addition of diethylaminosulfur trifluoride (DAST, 7 ul, 0.053 mmol). The reaction temperature was maintained at −78° C. for an hour and then slowly warmed to room temperature and stirred overnight. The reaction was quenched with 2.0 ml of saturated NaHCO3 solution and diluted with 6 ml CH2Cl2 and extracted three times. The combined organics were dried over Na2SO4, filtered and condensed. Crude product carried forward. Quantitative yield.

Workup

  1. customAn oven dried 20 ml scintillation vial
  2. customwas purged with N2
  3. additioncharged with anhydrous dichloromethane (1.5 ml, 0.018 M)
  4. temperatureslowly warmed to room temperature
  5. customThe reaction was quenched with 2.0 ml of saturated NaHCO3 solution
  6. additiondiluted with 6 ml CH2Cl2
  7. extractionextracted three times
  8. dry with materialThe combined organics were dried over Na2SO4
  9. filtrationfiltered
  10. customcondensed

Sources & evidence

ORD record
ord-bb1abd183f4849f6b20a65e76ea0a6d2
Source dataset
uspto-grants-2014_06
Patent number
US08748473B2

Reaction notes

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