Potassium Carbonate → N-(2,4-difluoro-3-[5-(1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-2,5-difluoro-benzenesulfonamide

HRID 60098Notes

Reaction equation

HRID 60098 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[CH:12]3)O1.Br[C:20]1[CH:21]=[C:22]2[C:28]([C:29]([C:31]3[C:32]([F:50])=[C:33]([NH:38][S:39]([C:42]4[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=4[F:49])(=[O:41])=[O:40])[CH:34]=[CH:35][C:36]=3[F:37])=[O:30])=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.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>[F:50][C:32]1[C:31]([C:29]([C:28]2[C:22]3[C:23](=[N:24][CH:25]=[C:20]([C:9]4[CH:10]=[C:11]5[C:15](=[CH:16][CH:17]=4)[NH:14][N:13]=[CH:12]5)[CH:21]=3)[NH:26][CH:27]=2)=[O:30])=[C:36]([F:37])[CH:35]=[CH:34][C:33]=1[NH:38][S:39]([C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=1[F:49])(=[O:40])=[O:41]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 177504691H-Indazole-5-boronic acid pinacol esterHCID 58368867N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide

Product 1

HCID 53261782N-(2,4-difluoro-3-[5-(1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-2,5-difluoro-benzenesulfonamideYield 55%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

Into a microwave vial, 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (12, 28 mg, 0.11 mmol) is combined with N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-2,5-difluoro-benzenesulfonamide (26, 50 mg, 0.09 mmol), tetrakis(triphenylphosphine)palladium(0) (2.2 mg, 0.0019 mmol), and potassium carbonate (1.0 mL, 1.0 M in water) in 3 mL of acetonitrile. The reaction is heated at 140° C. for 50 minutes in a microwave, the solvents removed under vacuum, and the residue purified by silica gel column chromatography, eluting with dichloromethane and methanol. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound as a white solid (P-0002, 28 mg, 50%). MS (ESI) [M+H+]+=565.85.

Workup

  1. customthe solvents removed under vacuum
  2. customthe residue purified by silica gel column chromatography
  3. washeluting with dichloromethane and methanol
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-07b4dd6627ce4bbca7612c3eb7b602c7
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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