Trifluoroacetic acid → 5-(3-Methoxyphenyl)-4-(piperazin-1-yl)-1h-pyrrolo[2,3-b]pyridine

HRID 79533Notes

Reaction equation

HRID 79533 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68762618tert-Butyl 4-(5-(3-methoxyphenyl)-1H-pyrrolo [2,3-b]pyri din-4-yl)piperazine-1-carboxylate

Product 1

HCID 687616565-(3-Methoxyphenyl)-4-(piperazin-1-yl)-1h-pyrrolo[2,3-b]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazine-1-carboxylate (0.111 g, 0.272 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was then added, and the reaction was stirred at room temperature for 2 hours. The reaction was then concentrated to dryness, dissolved in minimal DCM, and added dropwise to a stirring solution of 1M HCl in ether. The solid product was filtered, washed with ether, and dried to give 5-(3-methoxyphenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine (0.083 g, 99% yield) as the dihydrochloride salt.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutiondissolved in minimal DCM
  3. additionadded dropwise to a stirring solution of 1M HCl in ether
  4. filtrationThe solid product was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-268591f453744f69bdf07a844fd14558
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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