Potassium Carbonate → HCID 90412716, compound

HRID 1522013Notes

Reaction equation

HRID 1522013 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.[F:21][C:22]1[CH:23]=[CH:24][C:25]([O:31][CH3:32])=[C:26](B(O)O)[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([O:31][CH3:32])=[C:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([S:11]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=23)[CH:23]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 378186494-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90412716HCID 90412716, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromo-1-(4-methylphenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (100 g, 284.7 mmol) and (5-fluoro-2-methoxyphenyl)boronic acid (58.05 g, 341.6 mmol) in dimethoxyethane (1600 mL) and water (440 mL) was added potassium carbonate (106.2 g, 768.6 mmol). The mixture was purged with nitrogen and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane adduct (13.95 g, 17.08 mmol) was added. The mixture was purged with nitrogen for 10 minutes and stirred at 100° C. for 1 hour. After concentration, the residue was diluted with ethyl acetate (1500 mL) and washed with aqueous sodium bicarbonate (twice) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 30-60% ethyl acetate in petroleum ether to afford the title compound.

Workup

  1. additionwas added
  2. customThe mixture was purged with nitrogen for 10 minutes
  3. concentrationAfter concentration
  4. additionthe residue was diluted with ethyl acetate (1500 mL)
  5. washwashed with aqueous sodium bicarbonate (twice) and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel eluting with 30-60% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-25b6239f407b4917981163725fbe5e3d
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…