HCID 66801667, compound → HCID 66801420, compound

HRID 2366291Notes

Reaction equation

[Cl: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]>[Cl: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]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Iron powder (7.95 g, 141 mmol) was added to a solution of 2-(2-chloro-6-nitrophenyl)-7-fluorothiazolo[5,4-c]pyridine (4.35 g, 14.1 mmol) in AcOH (130 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 0-5% MeOH in DCM to afford the title compound as a yellow solid (3.63 g, 92% yield). 1H NMR (300 MHz, CDCl3): δ 9.03 (s, 1H), 8.52 (d, J=2.4 Hz, 1H), 7.16 (t, J=8.2 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H), 6.75 (d, J=8.3 Hz, 1H), 6.28 (br s, 2H). LCMS (Method D): RT=3.51 min, m/z: 280 [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 0-5% MeOH in DCM

Sources & evidence

ORD record: ord-7b6ba3786ea74ff3b87d82cbc7899cfa
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

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