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

HRID 2390685Notes

Reaction equation

HRID 2390685 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.[OH-].[NH4+:13]>O1CCOCC1>[Br:1][C:2]1[C:6]2[C:7]([NH2:13])=[N:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 106811193-Bromo-4-chlorofuro[3,2-c]pyridine

Product 1

HCID 184507953-Bromofuro[3,2-c]pyridin-4-amineYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-bromo-4-chlorofuro[3,2-c]pyridine (7.0 g, 22 mmol), 38 wt % aqueous ammonium hydroxide (75 mL) and dioxane (75 mL) in a Parr mini-reactor was stirred at 150° C. for two days. The solvent was removed in vacuo and water (200 mL) was added to the residue. The mixture was adjusted to pH 12 with 2N NaOH (aq) extracted with ethyl acetate (5×100 mL). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give the title compound (4.6 g, 71%). 1H NMR (DMSO-d6, 400 MHz) 8.13 (s, 1H), 7.85 (d, 1H), 6.92 (d, 1H), 6.17-6.27 (bs, 2H); RP-HPLC (Conditions d) Rt 8.02 min.; MS: MH+ 213, 215.

Workup

  1. customThe solvent was removed in vacuo and water (200 mL)
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate (5×100 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0619af8d446041408e54b7093e770cf9
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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