Sodium Bicarbonate → 3-(4-Fluorophenyl)-1-Hydroxy-2-(Pyridin-4-Yl)-1h-Pyrrolo(3,2-B)Pyridine

HRID 429193Notes

Reaction equation

HRID 429193 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[C:29]([N+:30]([O-:32])=O)=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:9](OS(C(F)(F)F)(=O)=O)[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:29]3[N:30]([OH:32])[C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 54372060Trifluoromethanesulfonic acid 2-(4-fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)vinyl ester

Product 1

HCID 52882383-(4-Fluorophenyl)-1-Hydroxy-2-(Pyridin-4-Yl)-1h-Pyrrolo(3,2-B)PyridineYield 71.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of trifluoromethanesulfonic acid 2-(4-fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)vinyl ester (1.5 g, 3.20 mmol) in ethyl acetate (50 ml) was added stannous chloride dihydrate (2.89 g, 12.8 mmol) and the reaction mixture was warmed to 50° C. After 1 h, the warm solution was treated with saturated sodium bicarbonate solution (10 ml) and filtered through Celite. The filtrate was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuO. Purification by flash column chromatography (CH2Cl2−95% CH2Cl2/MeOH gradient) gave 3-(4-fluorophenyl)-1-hydroxy-2-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridine as a tan solid (700 mg).

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuO
  5. customPurification by flash column chromatography (CH2Cl2−95% CH2Cl2/MeOH gradient)

Sources & evidence

ORD record
ord-204284e016ff4d03a70b9c8c339c1e7c
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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