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Potassium Phosphate, Tribasic → (1R,5S,6R)-5-(difluoromethyl)-5-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

HRID 1526657
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HRID 1526657 반응식
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[CH:12][C:13]([F:27])=[C:14]([C@:16]2([CH:24]([F:26])[F:25])[C@@H:22]3[C@@H:20]([CH2:21]3)[O:19][C:18]([NH2:23])=[N:17]2)[CH:15]=1.[C:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[N:35][CH:36]=1)#[C:29][CH3:30]>O1CCOCC1.O.O.C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C>[F:25][CH:24]([F:26])[C@@:16]1([C:14]2[CH:15]=[C:10]([C:33]3[CH:34]=[N:35][CH:36]=[C:31]([C:28]#[C:29][CH3:30])[CH:32]=3)[CH:11]=[CH:12][C:13]=2[F:27])[C@@H:22]2[C@@H:20]([CH2:21]2)[O:19][C:18]([NH2:23])=[N:17]1
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참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 574164825-(1-Propynyl)pyridine-3-boronic Acid (contains varying amounts of Anhydride)HCID 90401254(1R,5S,6R)-5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

생성물 1

HCID 90413015(1R,5S,6R)-5-(difluoromethyl)-5-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine수율 74%

시약·촉매·용매

3
HCID 178482226HCID 178482226, 화합물촉매HCID 962Water용매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
110 °C

실험 절차

A microwave vial was charged with mixture of potassium phosphate (0.19 g, 0.90 mmol), (1R,5S,6R)-5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine (16f-B, 0.10 g, 0.30 mmol), (5-(prop-1-yn-1-yl)pyridin-3-yl)boronic acid (0.12 g, 0.75 mmol) and 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (10.56 mg, 0.015 mmol) in dioxane/water (2.0/0.5 mL). The reaction mixture was heated to 110° C. for 30 min in the microwave. The reaction mixture was then diluted with water and extracted with DCM three times. The combined organic extracts were washed with brine and dried over sodium sulfate. The filtrate was concentrated in vacuo and the crude material was purified by silica gel chromatography (0-100% EtOAc-DCM) to obtain the title compound as a white solid (82.3 mg, 74% yield). MS m/z=372 [M+H]+. Calculated for C20H16F3N3O: 371.4.

후처리

  1. extractionextracted with DCM three times
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude material was purified by silica gel chromatography (0-100% EtOAc-DCM)

출처 및 근거

ORD 기록
ord-43ea1044f7ad414ca637e1665872f32e
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085576B2

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