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

HRID 2089045노트

반응식

HRID 2089045 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a1927c06082c4a1b9bfd7e7d372a35fb
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435980B2

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