Sodium Hydroxide → 4-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-ol

HRID 2114011Notes

Reaction equation

HRID 2114011 reaction equation
C([O:7][C:8]1[C:9]([CH3:28])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][N:12]=[C:11]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[F:27])(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[F:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[O:17][C:11]1[C:10]2=[C:9]([CH3:28])[C:8]([OH:7])=[CH:16][N:15]2[N:14]=[CH:13][N:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 210816484-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate

Product 1

HCID 210816464-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-olYield 85.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate (80 mg, 0.2 mmol) in THF (1 mL) was added a solution of NaOH in MeOH/H2O (0.2 mL, 1 M). The solution turned red instantly. After 5 minutes, the reaction was quenched with EtOAc (5 mL) and H2O (5 mL). The organic layer was separated, dried with sodium sulfate and concentrated in vacuo to give the title compound (52 mg, 85%) as a yellow solid.

Workup

  1. customthe reaction was quenched with EtOAc (5 mL) and H2O (5 mL)
  2. customThe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1daa634c005a4ce1a0586922df31c69b
Source dataset
uspto-grants-2008_10
Patent number
US07432373B2

Reaction notes

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