Triethylamine → 3-(1H-indol-5-yl)-5-(4-((4-(2,2,2-trifluoroethyl)piperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 85074Notes

Reaction equation

HRID 85074 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:24]=[CH:23][C:22]([CH2:25][N:26]6[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]6)=[CH:21][CH:20]=5)[CH:17]=4)[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.CS(O[CH2:54][C:55]([F:58])([F:57])[F:56])(=O)=O>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:24]=[CH:23][C:22]([CH2:25][N:26]6[CH2:31][CH2:30][N:29]([CH2:54][C:55]([F:58])([F:57])[F:56])[CH2:28][CH2:27]6)=[CH:21][CH:20]=5)[CH:17]=4)[NH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5565652,2,2-Trifluoroethyl MethanesulfonateHCID 701157013-(1H-indol-5-yl)-5-(4-(piperazin-1-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 547649033-(1H-indol-5-yl)-5-(4-((4-(2,2,2-trifluoroethyl)piperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(1H-indol-5-yl)-5-(4-(piperazin-1-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (50 mg) was dissolved in THF (1 mL) and treated with triethylamine (13 uL), and 2,2,2-trifluoroethyl methanesulfonate (13 uL); the reaction was allowed to stir for approximately hours, diluted water and extracted with EtOAC and washed with 1 N sodium hydroxide, water and brine and evaporated. The product was suspended in MeOH and (2 mL) detosylated directly by the addition of 0.5 mL sodium hydroxide solution, heated to 50 C for one hour. The reaction was diluted with water, extracted with dichloromethane and purified by MPLC, on silica gel, eluting with methanol in dichloromethane to yield 6 mg of an analytical sample (490 M+H).

Workup

  1. extractiondiluted water and extracted with EtOAC
  2. washwashed with 1 N sodium hydroxide, water and brine
  3. customevaporated
  4. addition(2 mL) detosylated directly by the addition of 0.5 mL sodium hydroxide solution
  5. temperatureheated to 50 C for one hour
  6. additionThe reaction was diluted with water
  7. extractionextracted with dichloromethane
  8. custompurified by MPLC, on silica gel
  9. washeluting with methanol in dichloromethane
  10. customto yield 6 mg of an analytical sample (490 M+H)

Sources & evidence

ORD record
ord-54e61ce02f5a4f72a2ba994fe40a9371
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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