HCID 66801527, compound → HCID 66801682, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[C:11]1[S:12][C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:20])[C:18]=2[N:19]=1>CC(O)=O.[Fe]>[F:1][C:2]1[C:3]([C:11]2[S:12][C:13]3[CH:14]=[N:15][CH:16]=[C:17]([F:20])[C:18]=3[N:19]=2)=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Iron powder (8.29 g, 148 mmol) was added to a solution of 2-(2-fluoro-6-nitrophenyl)-7-fluorothiazolo[5,4-c]pyridine (4.33 g, 14.8 mmol) in AcOH (144 mL). The reaction mixture was heated at 100° C. for 30 minutes and then allowed to cool to room temperature. The volatiles were removed under reduced pressure and the resultant residue was dissolved in DCM/MeOH and filtered through Celite® washing the filter pad thoroughly with further DCM/MeOH. The filtrate was concentrated under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 0-2% MeOH in DCM, then triturated with DCM and then dried to afford the title compound as a yellow solid (2.23 g, 57% yield). LCMS (Method D): RT=3.62 min, m/z: 264 [M+H+].
Workup
- temperatureto cool to room temperature
- customThe volatiles were removed under reduced pressure
- dissolutionthe resultant residue was dissolved in DCM/MeOH
- filtrationfiltered through Celite®
- washwashing the filter pad thoroughly with further DCM/MeOH
- concentrationThe filtrate was concentrated under reduced pressure
- customthe resultant residue was purified by column chromatography on silica gel eluting with 0-2% MeOH in DCM
- customtriturated with DCM
- customdried
Sources & evidence
- ORD record
- ord-3d6290686a014acaafb36abef426124a
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697708B2
Reaction notes
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