Water → 4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 28920Notes

Reaction equation

HRID 28920 reaction equation
C([N:4]1[C:8]2=[N:9][CH:10]=[C:11]([F:14])[C:12](I)=[C:7]2[CH:6]=[CH:5]1)(=O)C.[CH2:15]([N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[C:19]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[N:18]1)[CH3:16].C(=O)(O)[O-].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[CH2:15]([N:17]1[CH:21]=[C:20]([C:12]2[C:11]([F:14])=[CH:10][N:9]=[C:8]3[NH:4][CH:5]=[CH:6][C:7]=23)[C:19]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[N:18]1)[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 689953481-ethyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 689971671-Acetyl-5-fluoro-4-iodo-7-azaindole

Product 1

HCID 689982384-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-acetyl-5-fluoro-4-iodo-1H-pyrrolo[2,3-b]pyridine (0.822 mmol), 1-ethyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.15 mmol), tetrakis(triphenylphosphine)palladium(0) (0.041 mmol), sodium bicarbonate (2.47 mmol), water (2 mL) and N,N-dimethylformamide (6 mL) were heated to 100° C. in a sealed tube for 16 h. The reaction mixture was quenched with water (5 mL) and extracted with ethyl acetate (3×10 mL). The combined extracts were dried over sodium sulfate filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (50% ethyl acetate/hexanes) to give the title compound as a yellow solid (80%). ESMS [M+H]+: 352.2

Workup

  1. customThe reaction mixture was quenched with water (5 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8e78e9a8cf8c4568933876e7f3b74e2c
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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