Potassium Carbonate → HCID 90411876, compound

HRID 1521951Notes

Reaction equation

HRID 1521951 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][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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:20][C:21]1[CH:26]=[CH:25][C:24]([O:30][CH3:31])=[C:23]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([S:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=23)[CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 90411876HCID 90411876, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (10.00 g, 29.7 mmol), 5-fluoro-2-methoxyphenylboronic acid (5.54 g, 32.6 mmol), 2M aqueous potassium carbonate (66.7 mL, 133 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.453 g, 1.779 mmol) in 1,2-dimethoxyethane (250 mL) was degassed with nitrogen and heated at 100° C. for 1.5 hours. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate (twice) and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using an ISCO Companion flash system eluting with heptane/ethyl acetate (75:25 to 60:40) to afford the title compound. MS (ESI+) m/z 383.1 (M+H)+.

Workup

  1. customwas degassed with nitrogen
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with aqueous sodium bicarbonate (twice) and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel using an ISCO Companion flash system
  8. washeluting with heptane/ethyl acetate (75:25 to 60:40)

Sources & evidence

ORD record
ord-54ac5afc515b42ad8b046b0ae061c570
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…