Potassium Carbonate → 4-(2-Fluoro-4-nitrophenoxy)-2-methyl-1H-pyrrolo[2,3-]pyridine

HRID 347562Notes

Reaction equation

HRID 347562 reaction equation
CC1N[C:5]2[N:6]=[CH:7][CH:8]=[C:9](O)[C:4]=2C=1.[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17]C=1F.[C:23](=[O:26])([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:23]=1[O:26][N:6]1[C:5]2=[CH:14][CH:15]([CH3:16])[NH:20][C:4]2=[CH:9][CH:8]=[CH:7]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178422234HCID 178422234, compound

Product 1

HCID 867603794-(2-Fluoro-4-nitrophenoxy)-2-methyl-1H-pyrrolo[2,3-]pyridineYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-methyl-1H-pyrrolo[2,3-b]pyridin-4-ol (90 mg, TFA salt, 0.34 mmol), 3,4-difluoronitrobenzene (0.05 mL) and potassium carbonate (100 mg, 0.72 mmol) in DMF (1 mL) was stirred at 50° C. for 2 h. The mixture was diluted with water and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water, dried (MgSO4) and concentrated in vacuo to afford the crude product, which was purified by preparative HPLC to give the title compound (45 mg, 46%). 1H NMR (CD3OD) δ 8.25 (dd, 2H, J=10.4, 2.6 Hz), 8.12 (m, 1H), 8.04 (d, 1H, J=5.5 Hz), 7.30 (t, 1H, J=8.3 Hz), 6.67 (d, 1H, J=5.5 Hz), 5.95 (s, 1H), 2.41 (s, 3H); MS(ESI+) m/z 288 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-04a3795dac184a56b213f4ac28192b81
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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