Methanol → Methyl 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 2117182Notes

Reaction equation

HRID 2117182 reaction equation
ClC(Cl)(Cl)C(C1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[F:24])[NH:7][CH:6]=1)=O.CO.C1COCC1.[OH-].[Na+].C[CH2:37][O:38][C:39]([CH3:41])=[O:40]>>[F:24][C:16]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=1[O:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:7][CH:6]=[C:41]([C:39]([O:38][CH3:37])=[O:40])[C:13]=12

Participants

6

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21081539HCID 21081539, compound

Product 1

HCID 21081729Methyl 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 61%

Procedure

To a solution of 2,2,2-trichloro-1-(4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone (490 mg, 1.17 mmol, See: Step A of Example 270) in a mixed solvent (10 mL of MeOH and 10 mL of THF) was added 1 N NaOH (10 mL, 10 mmol). The reaction mixture was stirred at room temperature for 3 h, and diluted with EtOAc (30 mL). The organic layer was washed with sat. aq. NaHCO3, solution, dried and concentrated in vacuo to give the desired product (235 mg, 61%) as a light brown solid. MS(ESI+) m/z 332.2 (M+H)+.

Workup

  1. washThe organic layer was washed with sat. aq. NaHCO3, solution
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36b1d0004c0a41a48997d3ade4a4fcd8
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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