Potassium Carbonate → N-[5-Chloro-2-(1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-pyridin-3-yl]-4-ethyl-3-trifluoromethyl-benzenesulfonamide

HRID 1898289Notes

Reaction equation

HRID 1898289 reaction equation
Br[C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:24])=[CH:4][N:3]=1.[NH:25]1[C:29]2[N:30]=[CH:31][CH:32]=[C:33](B(O)O)[C:28]=2[CH:27]=[CH:26]1.[C:37](=O)([O-])[O-:38].[K+].[K+].[C]=O>C1(OC)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:24][C:5]1[CH:6]=[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)(=[O:11])=[O:10])[C:2]([C:37]([C:33]2[C:28]3[CH:27]=[CH:26][NH:25][C:29]=3[N:30]=[CH:31][CH:32]=2)=[O:38])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 497589941H-Pyrrolo(2,3-b)pyridin-4-ylboronic acidHCID 58268075N-(2-Bromo-5-chloro-pyridin-3-yl)-4-ethyl-3-trifluoromethyl-benzenesulfonamideHCID 178418416HCID 178418416, compound

Product 1

HCID 44178159N-[5-Chloro-2-(1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-pyridin-3-yl]-4-ethyl-3-trifluoromethyl-benzenesulfonamideYield 3.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 7519AnisoleSolvent

Procedure

A solution/suspension made of 97 mg (0.22 mmol) of N-(2-bromo-5-chloro-pyridin-3-yl)-4-ethyl-3-trifluoromethyl-benzenesulfonamide, 140 mg (0.87 mmol) of 1H-pyrrolo[2,3-b]pyridine-4-boronic acid (mixture with its neopentyl glycolate ester and 1H-pyrrolo[2,3-b]pyridine), 240 mg (1.74 mmol) of potassium carbonate and 15 mg (0.022 mmol) of bis(triphenylphosphine)dichloropalladium(II) in 1 mL of anisole was stirred at 150° C. under 10 atm pressure of carbon monoxide for 2 h. After cooling down and decompression the mixture was introduced onto a flash column and eluted with 50-100% ethyl acetate in hexanes. Fractions containing the product were repurified on reverse-phase HPLC and free based to give 3.5 mg of the product as a yellow solid. LC-MSD, m/z for C22H16ClF3N4O3S [M+H]+=509.0, 511.0.

Workup

  1. temperatureAfter cooling down
  2. additiondecompression the mixture was introduced onto a flash column
  3. washeluted with 50-100% ethyl acetate in hexanes
  4. additionFractions containing the product
  5. customwere repurified on reverse-phase HPLC

Sources & evidence

ORD record
ord-1d02647b3d3f49ab936a38f0bbabc093
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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