Ammonia → 3-Bromofuro[3,2-c]pyridin-4-amine

HRID 734306Notes

Reaction equation

HRID 734306 reaction equation
[Br:1][C:2]1[C:6]2[C:7](Cl)=[N:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[NH3:12].C(OCC)(=O)C>O1CCOCC1.[Cl-].[Na+].O>[Br:1][C:2]1[C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 106811193-Bromo-4-chlorofuro[3,2-c]pyridine

Product 1

HCID 184507953-Bromofuro[3,2-c]pyridin-4-amine

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

To the solution of 3-bromo-4-chloro-furo[3,2-c]pyridine (3.0 g) in 40 ml of dioxane was added 28% ammonia solution (15 ml) in an autoclave and put into the oil bath. The reaction mixture was allowed to heat up to 150° C. and stir for 5 days at 150° C. The resultant mixture was poured into ethyl acetate and brine. The organic phases was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on a silica gel column to afford 3-bromo-furo[3,2-c]pyridin-4-ylamine (1.3 g). 1H NMR (400 MHz, CDCl3) ppm 7.93 (d, J=6.1 Hz, 1H), 7.52 (s, 1H), 6.87 (d, J=5.8 Hz, 1H). MS: m/z 213, 215 (M+H)+.

Workup

  1. customThe organic phases was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2605b6d7e9534c5fa568433e3c927f9c
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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