Hydrochloric Acid → 2-Chloro-3-methylfuro[2,3-c]pyridin-7-amine
Reaction equation
[Cl:1][C:2]1[O:25][C:5]2=[C:6]([N:10](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:26].Cl.O1CCOCC1>>[Cl:1][C:2]1[O:25][C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:26]Participants
Conditions
- Temperature
- 55 °C
Procedure
Di-tert-butyl (2-chloro-3-methylfuro[2,3-c]pyridin-7-yl)imidodicarbonate (3.2 g, 8.38 mmol) DCM (25 mL) was cooled in an ice bath and treated with 4 N HCl in 1,4-dioxane (12.5 mL, 50 mmol) added slowly over several minutes. The reaction was removed from the cooling bath and heated at 55° C. for 16 h. The mixture was concentrated in vacuo and the residue was suspended in DCM and treated with saturated NaHCO3 until the pH reached ˜8.5. The organic layer was washed with water, then brine and then dried over anhydrous Na2SO4. After concentration in vacuo, the material was purified by flash chromatography (3% MeOH:DCM) to provide 1.0 g (66%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.87 (d, J=5.4 Hz, 1H), 6.79 (d, J=5.4 Hz, 1H), 4.78 (br s, 2H), 2.16 (s, 3H).
Workup
- additionadded slowly over several minutes
- customThe reaction was removed from the cooling bath
- concentrationThe mixture was concentrated in vacuo
- additiontreated with saturated NaHCO3 until the pH
- washThe organic layer was washed with water
- dry with materialbrine and then dried over anhydrous Na2SO4
- concentrationAfter concentration in vacuo
- customthe material was purified by flash chromatography (3% MeOH:DCM)
Sources & evidence
- ORD record
- ord-1508e79fda6a436b885dbbdb9fd3a703
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
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