Formaldehyde → HCID 59428333, compound

HRID 503939Notes

Reaction equation

HRID 503939 reaction equation
C=O.[C:3]([BH3-])#[N:4].[Na+].FC(F)(F)C(O)=O.[C:14]1([S:20]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([F:32])=[CH:29][CH:30]=3)[C:25]([S:33]([C:36]3[CH:41]=[CH:40][C:39]([CH:42]4[CH2:46][CH2:45]N[CH2:43]4)=[C:38]([CH3:47])[CH:37]=3)(=[O:35])=[O:34])=[CH:24]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>C(#N)C>[C:14]1([S:20]([N:23]2[C:31]3[C:26](=[CH:27][C:28]([F:32])=[CH:29][CH:30]=3)[C:25]([S:33]([C:36]3[CH:41]=[CH:40][C:39]([CH:42]4[CH2:46][CH2:45][N:4]([CH3:3])[CH2:43]4)=[C:38]([CH3:47])[CH:37]=3)(=[O:34])=[O:35])=[CH:24]2)(=[O:21])=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 66877625HCID 66877625, compound

Product 1

HCID 59428333HCID 59428333, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Formaldehyde (37% in water, 0.19 mL, 2.505 mmol) and sodium cyanoborohydride (63 mg, 1.002 mmol) were added to a solution of 1-benzenesulfonyl-5-fluoro-3-(3-methyl-4-pyrrolidin-3-yl-benzenesulfonyl)-1H-indole trifluoroacetate (0.305 mg, 0.5011 mmol) in acetonitrile (3 mL). The reaction mixture was stirred at room temperature for 2 hours, then buffered to pH 12 by addition of 1 M aqueous NaOH. The mixture was extracted with DCM, and the combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (DCM/MeOH(NH4OH) to give 0.209 g (81% yield) of 1-benzenesulfonyl-5-fluoro-3-[3-methyl-4-(1-methyl-pyrrolidin-3-yl)-benzenesulfonyl]-1H-indole as a white foam. MS (M+H)=513.

Workup

  1. extractionThe mixture was extracted with DCM
  2. washthe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting crude material was purified via flash chromatography (DCM/MeOH(NH4OH)

Sources & evidence

ORD record
ord-adb586cbe59545b49d2d8988c3765864
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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