(2-Amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester → HCID 86614490, compound
Reaction equation
C([O:3][C:4](=O)[N:5]([C:13]1[CH:18]=[C:17]([Br:19])[N:16]=[C:15]([NH2:20])[C:14]=1[N+:21]([O-])=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C>CC(O)=O.CCOC(C)=O.O.[Fe]>[NH2:20][C:15]1[C:14]2[NH:21][C:4](=[O:3])[N:5]([CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:18]=[C:17]([Br:19])[N:16]=1Participants
6
Procedure
(2-Amino-6-bromo-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester (50 mg, 0.13 mmol) was dissolved in AcOH (3 ml). Fe powder (43 mg, 0.76 mmol) was added and the mixture was vigorously stirred at room temperature for 24 h. The reaction mixture diluted with EtOAc (20 ml) and water (10 ml). The mixture was filtered through celite, washing through with EtOAc (20 ml). The layers were separated and the organic layer was washed with water (10 ml), sat. NaHCO3 (aq) (2×10 ml) and brine (10 ml), dried over MgSO4 and concentrated in vacuo. The crude was triturated in pentane, filtered and dried in vacuo at 40° C. to give the title compound (15 mg) as a beige solid.
Workup
- filtrationThe mixture was filtered through celite
- washwashing through with EtOAc (20 ml)
- customThe layers were separated
- washthe organic layer was washed with water (10 ml), sat. NaHCO3 (aq) (2×10 ml) and brine (10 ml)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude was triturated in pentane
- filtrationfiltered
- customdried in vacuo at 40° C.
Sources & evidence
- ORD record
- ord-30cdc55b88e345469bdb971dedba6230
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691877B2
Reaction notes
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