Aniline → 1-[(4-methylphenyl)sulphonyl]-N-phenyl-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 1878636Notes

Reaction equation

HRID 1878636 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:3]=[C:4]3[CH:10]=[CH:9]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-

Product 1

HCID 671317181-[(4-methylphenyl)sulphonyl]-N-phenyl-1H-pyrrolo[2,3-b]pyridin-5-amineYield 172.7%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

Put 750 mg of 5-bromo-1-[(4-methylphenyl)sulphonyl]-1H-pyrrolo[2,3-b]pyridine in 19 cm3 of toluene, 54 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 970 mg of caesium carbonate, 280 mg of aniline and 40 mg of tri(dibenzylideneacetone)dipalladium(0) in a microwave oven reactor. Irradiate the reactor in a microwave oven for forty-five minutes at 150° C. After cooling, filter the reaction mixture, then reduce to dryness under vacuum in a rotary evaporator. Combine the brown residue with another two residues obtained similarly, then purify by flash chromatography on a silica column with dichloromethane eluent to give 1.34 g of 1-[(4-methylphenyl)sulphonyl]-N-phenyl-1H-pyrrolo[2,3-b]pyridin-5-amine in the form of a beige powder with the following physical characteristics:

Workup

  1. customIrradiate the reactor in a microwave oven for forty-five minutes at 150° C
  2. temperatureAfter cooling
  3. filtrationfilter the reaction mixture
  4. customreduce to dryness under vacuum in a rotary evaporator
  5. customobtained similarly
  6. custompurify by flash chromatography on a silica column with dichloromethane eluent

Sources & evidence

ORD record
ord-a4ec31543336465fb57592e270d4f6f3
Source dataset
uspto-grants-2012_11
Patent number
US08314121B2

Reaction notes

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