Sodium hydride → (4aS,7aR)-1-(5-Phenylethynyl-pyridin-2-yl)-hexahydro-cyclopenta[d][1,3]oxazin-2-one

HRID 1507134노트

반응식

HRID 1507134 반응식
[NH:1]1[C@@H:6]2[CH2:7][CH2:8][CH2:9][C@@H:5]2[CH2:4][O:3][C:2]1=[O:10].F[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][N:13]=1.[H-].[Na+]>CN(C=O)C>[C:20]1([C:19]#[C:18][C:15]2[CH:16]=[CH:17][C:12]([N:1]3[C@@H:6]4[CH2:7][CH2:8][CH2:9][C@@H:5]4[CH2:4][O:3][C:2]3=[O:10])=[N:13][CH:14]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 117871704(4aS,7aR)-Hexahydro-cyclopenta[d][1,3]oxazin-2-oneHCID 1178732652-Fluoro-5-phenylethynylpyridine

생성물 1

HCID 73670555(4aS,7aR)-1-(5-Phenylethynyl-pyridin-2-yl)-hexahydro-cyclopenta[d][1,3]oxazin-2-one수율 23.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a 10 ml Round bottomed flask were dissolved (4aS,7aR)-hexahydro-cyclopenta[d]-[1,3]oxazin-2-one (80 mg, 0.57 mmol, 1.0 equiv.) and 2-fluoro-5-(phenylethynyl)pyridine (112 mg, 0.57 mmol, 1.0 equiv.) in 2 ml of DMF. Sodium hydride (60% suspension) (29.5 mg, 0.74 mmol, 1.3 equiv.) were added and the brown suspension was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted twice with ethyl acetate. The combined organic phases were dried, filtered and concentrated. The crude material was purified by flash chromatography over a prepacked silica column eluting with 0-50% ethyl acetate in heptane gradient to yield 42.5 mg of the title compound as colorless amorphous solid, MS: m/e=319.1 (M+H+).

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted twice with ethyl acetate
  3. customThe combined organic phases were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography over a prepacked silica column
  7. washeluting with 0-50% ethyl acetate in heptane gradient

출처 및 근거

ORD 기록
ord-e7e1a687cbd94d2d98c06eb9105cb46d
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221802B2

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