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

HRID 2114013
Notes
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Reaction equation

HRID 2114013 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 210816534-(2-Fluoro-4-nitrophenoxy)-6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 210816183-Fluoro-4-(6-methoxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst
HCID 8028TetrahydrofuranSolvent

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

  1. filtrationThe solution was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. customThe product mixture was purified by a SCX cartridge (
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes