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Tetrahydrofuran → 4-((1RS,2RS)-2-(4-chlorophenyl)-3-(trimethylsilyl)cyclopropyl)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203079
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HRID 2203079 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[N:13]([CH3:19])[C:12]=3[CH:20]=2)[C:4](=[O:21])[CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH:31](B3OC(C)(C)C(C)(C)O3)[CH:30]2[Si:41]([CH3:44])([CH3:43])[CH3:42])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C1COCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]2[CH:30]([Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:31]2[C:2]2[CH:7]=[CH:6][N:5]([C:8]3[CH:9]=[CH:10][C:11]4[N:15]=[C:14]([CH:16]5[CH2:18][CH2:17]5)[N:13]([CH3:19])[C:12]=4[CH:20]=3)[C:4](=[O:21])[CH:3]=2)=[CH:27][CH:28]=1
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참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-oneHCID 131735783((2RS,3SR)-2-(4-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)(trimethyl)silane

생성물 1

HCID 1317357844-((1RS,2RS)-2-(4-chlorophenyl)-3-(trimethylsilyl)cyclopropyl)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one
수율 17%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

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온도
70 °C

실험 절차

A mixture of 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (108 mg), ((2RS,3SR)-2-(4-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)(trimethyl)silane (110 mg), potassium carbonate (130 mg), PdCl2(dppf) (11.5 mg), THF (6 ml) and water (2.0 ml) was heated at 70° C. overnight. The mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (26.0 mg) as a white solid.

후처리

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-b019c31b49354d59b69fa50fbd29b8cb
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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