Cesium carbonate → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol

HRID 1392385노트

반응식

HRID 1392385 반응식
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].Br[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[C:38]([F:41])([F:40])[F:39].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.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]>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[C:38]([F:39])([F:41])[F:40])[CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 5209832-Bromo-5-fluorobenzotrifluorideHCID 115679944-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride

생성물 1

HCID 693116644-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To the suspension of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride (300 mg) obtained in Step 2 of Example 1 in 5 ml of toluene, were added 1-bromo-4-fluoro-2-trifluoromethylbenzene (0.198 ml), cesium carbonate (1.42 g), (S)-2,2-bis(diphenylphospino)-1,1-binaphtyl (BINAP; 45.4 mg) and tris(dibenzylideneacetone)dipalladium (1.42 g). The reaction mixture was stirred for about 4 hours at 100° C. under nitrogen atmosphere, was diluted with 30 ml of ethyl acetate, filtered, and concentrated. The resulting residue was purified with column chromatography to give 179 mg of the titled compound.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe resulting residue was purified with column chromatography

출처 및 근거

ORD 기록
ord-28949b92e49a4da1baaf12636fa823fc
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342027B2

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