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

HRID 347455
Notes
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Reaction equation

HRID 347455 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-cb3044ff02144e8da545f61e9de36df0
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173031B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes