Methanol → 3-Fluoro-4-(6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

HRID 2114013Notes

Reaction equation

[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:16])[C:12]([O:14][CH3:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.CO.[NH4+].[Cl-]>C1COCC1.[Zn]>[F:1][C:2]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:16])[C:12]([O:14][CH3:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazine (35 mg, 0.11 mmol) in THF (1.0 mL) was added MeOH (1.0 mL) followed by Zn (100 mg, 1.5 mmol) and NH4Cl (43 mg, 0.80 mmol). The reaction was heated at 60° C. for 3 h. The solution was filtered through Celite® and concentrated in vacuo. The product mixture was purified by a SCX cartridge (eluted with ammonia in methanol (2 M) to give the title compound (15 mg, 50%) as a white solid.

Workup

filtrationThe solution was filtered through Celite®
concentrationconcentrated in vacuo
customThe product mixture was purified by a SCX cartridge (
washeluted with ammonia in methanol (2 M)

Sources & evidence

ORD record: ord-ccf9aada13254710afc5acc6ade2a75b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432373B2

Reaction notes

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