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Cesium carbonate → Benzyl 3-oxo-4-(2-(trifluoromethyl)pyridin-4-yl)-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate

HRID 572425
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HRID 572425 반응식
[O:1]=[C:2]1[NH:7][CH:6]2[CH:4]([CH2:5]2)[N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Br[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>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].O1CCOCC1>[O:1]=[C:2]1[N:7]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH:6]2[CH:4]([CH2:5]2)[N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2802741Benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylateHCID 234369504-Bromo-2-(trifluoromethyl)pyridine

생성물 1

HCID 70982114Benzyl 3-oxo-4-(2-(trifluoromethyl)pyridin-4-yl)-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate수율 74%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

Using analogous reagents and reaction conditions as described in Example 1 above, benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate (100 mg, 0.43 mmol) was heated with 4-bromo-2-(trifluoromethyl)pyridine (107 mg, 0.474 mmol), xantphos (22.36 mg, 0.038 mmol), Pd2(dba)3 (12 mg, 0.012 mmol), cesium carbonate (210 mg, 0.64 mmol) and 1,4-dioxane (6.0 mL) at 100° C. for 1 hour to yield the crude product. Purification by column chromatography on silica gel (35% ethyl acetate in hexane) afforded 120 mg of the product (74% yield).

후처리

  1. customreagents and reaction conditions
  2. customto yield the crude product
  3. customPurification by column chromatography on silica gel (35% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-c6da7eaf35dc404da130e6cf938d5912
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029399B2

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