Sodium Hydroxide → HCID 68995250, compound

HRID 28961Notes

Reaction equation

HRID 28961 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14](S(C4C=CC=CC=4)(=O)=O)[C:15]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[CH:19][CH:18]=4)=[CH:16][C:9]=23)[C:5]([C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-])=O)=[CH:40][CH:39]=2)=[N:4]1)[CH3:2].[OH-].[Na+]>C(O)(=O)C.[Zn]>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH:18]=[CH:19][C:20]([CH2:23][N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[CH:21][CH:22]=4)=[CH:16][C:9]=23)[C:5]([C:38]2[CH:39]=[CH:40][C:41]([NH2:44])=[CH:42][CH:43]=2)=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 689982174-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-[4-(1-pyrrolidinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68995250HCID 68995250, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-[4-(1-pyrrolidinylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine (0.487 mmol) in glacial acetic acid (4 mL) was added zinc powder (3.41 mmol). After 1 h, the reaction was filtered and the zinc residue was rinsed with acetic acid. The filtrate was concentrated under reduced pressure and azeotroped five times with 1:1 methanol/toluene to remove residual acetic acid. The crude aniline was dissolved in methanol, treated with 6N NaOH (1.46 mmol) and heated to 70° C. After 5 h, the reaction mixture was concentrated under reduced pressure and the residue was suspended in cold water and stirred vigorously. The precipitate was collected by filtration and dried to constant weight under high vacuum to give title compound. ESMS [M+H]+: 463.4

Workup

  1. filtrationthe reaction was filtered
  2. washthe zinc residue was rinsed with acetic acid
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customazeotroped five times with 1:1 methanol/toluene
  5. customto remove residual acetic acid
  6. dissolutionThe crude aniline was dissolved in methanol
  7. waitAfter 5 h
  8. concentrationthe reaction mixture was concentrated under reduced pressure
  9. filtrationThe precipitate was collected by filtration
  10. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-a85b9e4b6b984eaca8a331e89b48ba1d
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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