Ammonium Hydroxide → 3-Bromofuro[3,2-c]pyridin-4-amine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was removed in vacuo and water (200 mL)
- additionwas added to the residue.The mixture
- extractionextracted with ethyl acetate (5×100 mL)
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-5b3ae522fb1045d29a60742cbf7b7f0c
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202363B2
Reaction notes
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