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

HRID 1986062Notes

Reaction equation

HRID 1986062 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+]>O1CCCC1.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 tetrahydrofuran (5 mL) and methanol (10 mL), was 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 resulting residue was purified by flash column chromatography (silica gel, 1-5% MeOH in CH2Cl2) to afford the desired product (205 mg, 77%) as an off-white solid. 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 resulting residue was purified by flash column chromatography (silica gel, 1-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-08b8b5b5508b45b697c852dfbd35ba57
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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