4-[1-{[4-(methyloxy)phenyl]methyl}-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine → HCID 178526567, compound

HRID 28929Notes

Reaction equation

HRID 28929 reaction equation
COC1C=CC(C[N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[NH:21][CH:22]=[CH:23][C:16]=34)[C:12]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[N:11]2)=CC=1>FC(F)(F)C(O)=O.O>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([C:12]2[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[NH:21][CH:22]=[CH:23][C:16]=34)=[CH:14][NH:10][N:11]=2)=[CH:29][CH:28]=1)([O-:32])=[O:31]

Participants

4

Reactant 1

HCID 689992594-[1-{[4-(methyloxy)phenyl]methyl}-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178526567HCID 178526567, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[1-{[4-(methyloxy)phenyl]methyl}-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine (0.22 mmol) in trifluoroacetic acid (0.75 mL) was heated at 74° C. for 1.5 h. The reaction mixture was diluted with water (4 mL) and extracted with (3×5 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and were concentrated. Purification of the residue by Gilson reverse phase HPLC afforded the title product as a yellow solid (64%). ESMS [M+H]+: 306.4

Workup

  1. extractionextracted with (3×5 mL) ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationwere concentrated
  4. customPurification of the residue by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-e023cb592ee34f3ba521d36c151ce216
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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