Ammonium Chloride → 4-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

HRID 2377733Notes

Reaction equation

HRID 2377733 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][CH:12]=[CH:13][C:6]=12.[Cl-].[NH4+]>C1COCC1.CO.[Zn]>[NH:11]1[C:7]2=[N:8][CH:9]=[CH:10][C:5]([O:4][C:3]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:2]=3[F:1])=[C:6]2[CH:13]=[CH:12]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 210816364-(2-Fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroanilineYield 77%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine (300 mg, 1.1 mmol) in THF (5 mL) and methanol (10 mL), were added zinc powder (350 mg, 5.5 mmol) and ammonium chloride (294 mg, 5.5 mmol). The mixture was stirred at rt overnight. The mixture was filtered through a pad of Celite®, rinsed with methanol. The filtrate was concentrated in vacuo and the product was purified by flash column chromatography (silica gel, 1-5% MeOH in CH2Cl2) to afford the desired product (205 mg, 77% yield) as an off-white solid. LC/MS (ESI+) m/z 244 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe product was purified by flash column chromatography (silica gel, 1-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6c68701c9f874ea08b35feabcd5354ca
Source dataset
uspto-grants-2008_12
Patent number
US07470693B2

Reaction notes

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