Bicarbonate Ion → N-[2-Fluoro-3-(3,6-dibromo-9H-carbazole-9-yl)propyl]-N-(3-methoxyphenyl)trifluoromethanesulfonamide

HRID 1028276Notes

Reaction equation

HRID 1028276 reaction equation
C1N(S(F)(F)[F:8])CCOC1.[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH2:26][CH:27](O)[CH2:28][N:29]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44]C)[CH:38]=3)[S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[C:17]3[C:22]([C:23]=2[CH:24]=1)=[CH:21][C:20]([Br:25])=[CH:19][CH:18]=3.C(=O)(O)[O-]>C(Cl)Cl>[Br:25][C:20]1[CH:19]=[CH:18][C:17]2[N:16]([CH2:26][CH:27]([F:8])[CH2:28][N:29]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[CH:38]=3)[S:30]([C:33]([F:34])([F:35])[F:36])(=[O:32])=[O:31])[C:15]3[C:23]([C:22]=2[CH:21]=1)=[CH:24][C:12]([Br:11])=[CH:13][CH:14]=3

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 2733258Morpholinosulfur trifluorideHCID 71254252N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-1,1,1-trifluoro-N-(3-ethoxyphenyl)methanesulfonamide

Product 1

HCID 72163772N-[2-Fluoro-3-(3,6-dibromo-9H-carbazole-9-yl)propyl]-N-(3-methoxyphenyl)trifluoromethanesulfonamideYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Morpho-Dast (14.0 ml, 115 mmol) was added to a solution of N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-1,1,1-trifluoro-N-(3-ethoxyphenyl)methanesulfonamide (20.6 g, 32.4 mmol) in anhydrous methylene chloride (315 ml) and stirred overnight. The solution, in a water bath at ambient temperature, was neutralized by dropwise addition of 375 ml saturated bicarbonate solution. The biphasic mixture was extracted with methylene chloride twice. The combined organics were dried over MgSO4, filtered and condensed to give 21.5 g of off-white foam in quantitative yield.

Workup

  1. extractionThe biphasic mixture was extracted with methylene chloride twice
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. customcondensed

Sources & evidence

ORD record
ord-7907d1f2e09649888d756845fa387260
Source dataset
uspto-grants-2014_05
Patent number
US08735440B2

Reaction notes

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