Trifluoroacetic acid → 5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 715046Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)[CH:18]=4)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:30][N:27]1[CH2:26][CH2:25][N:24]([CH2:23][C:19]2[CH:18]=[C:17]([C:15]3[CH:16]=[C:11]4[CH:10]=[CH:9][NH:8][C:12]4=[N:13][CH:14]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine (151) (30 mg) in CHCl3 (8 mL) was added trifluoroacetic acid (5 mL) and heated at 50° C. for 12. After completion of the reaction the solvents were removed, diluted with cold water, pH was adjusted to 8 and the aqueous phase extracted with CHCl3 twice. The organic layer was washed with brine solution and dried over sodium sulphate and the solvent completely distilled off to get the crude product. The crude was passed through 100-200 mesh silica gel, eluting the pure compound in 2% MeOH/CHCl3 gave pale yellow solid compound 5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine 152.

Workup

customAfter completion of the reaction the solvents
customwere removed
additiondiluted with cold water, pH
extractionthe aqueous phase extracted with CHCl3 twice
washThe organic layer was washed with brine solution
dry with materialdried over sodium sulphate
distillationthe solvent completely distilled off
customto get the crude product
washeluting the pure compound in 2% MeOH/CHCl3

Sources & evidence

ORD record: ord-f427f490103e4af5a10683548c8a6787
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187473B2

Reaction notes

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