Aniline → 3-(2-chloro-6-(cyclohexylamino)pyridin-4-yl)-N-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 2089045Notes

Reaction equation

HRID 2089045 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:12]=3)=[CH:9][N:8]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:5]2=[N:6][CH:7]=1.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:17][C:15]1[CH:16]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:3]=3)[N:8]([S:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)(=[O:26])=[O:27])[CH:9]=2)[CH:12]=[C:13]([NH:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N:14]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

Product 1

HCID 871925973-(2-chloro-6-(cyclohexylamino)pyridin-4-yl)-N-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 12.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 171a (0.200 g, 0.366 mmol), aniline (0.044 g, 0.476 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (X-PHOS) (0.009 g, 0.018 mmol), catalytic tris(dibenzylideneacetone)dipalladium (0) and potassium carbonate (0.127 g, 0.916 mmol) in 4 mL tert-butanol was heated at 110° C. for 16 hours. The material was cooled to room temperature, diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (20% ethyl acetate/hexane) to afford 0.025 gm of the title compound. m/z 558.0 (APCI, M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel using flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a1927c06082c4a1b9bfd7e7d372a35fb
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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