Sodium Bicarbonate → 4-(5-fluoro-2-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 1522001Notes

Reaction equation

HRID 1522001 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[N:10]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[CH:12][C:3]=12.[F:22][C:23]1[CH:24]=[CH:25][C:26]([O:32][CH3:33])=[C:27](B(O)O)[CH:28]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.O.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl>[F:22][C:23]1[CH:28]=[CH:27][C:26]([O:32][CH3:33])=[C:25]([C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]3[N:10]([S:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:15])=[O:14])[CH:11]=[CH:12][C:3]=23)[CH:24]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 90413564HCID 90413564, compound

Product 1

HCID 904117294-(5-fluoro-2-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Example 236A (2 g, 6.29 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (1.284 g, 7.55 mmol), sodium hydrogencarbonate (1.586 g, 18.88 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II)-dichloromethane adduct (0.276 g, 0.378 mmol) in 80 mL N,N-dimethylformamide and 20 mL water was degassed with nitrogen and heated at 100° C. for 3 hours. The mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica-gel flash chromatography (AnaLogix IntelliFlash 280) eluting with dichloromethane afforded the title compound. MS (ESI+) m/z 408 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica-gel flash chromatography (AnaLogix IntelliFlash 280)
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-55b2033a35f843d68fe2216dd02bc631
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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