Cesium fluoride → 2-(((2S,3R)-1-(3-Fluoro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

HRID 61181노트

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HRID 61181 반응식
[F:1][C:2]1[C:3](I)=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]([CH3:13])[C@H:8]1[CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])=[O:6].C([Sn](CCCC)(CCCC)[C:35]1[N:40]=[CH:39][CH:38]=[CH:37][N:36]=1)CCC.[F-].[Cs+]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[C:3]([C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]([CH3:13])[C@H:8]1[CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])=[O:6]

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 1177278122-(((2S,3R)-1-(3-Fluoro-2-iodobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

생성물 1

HCID 1177279782-(((2S,3R)-1-(3-Fluoro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione수율 75%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 2-(((2S,3R)-1-(3-fluoro-2-iodobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (0.493 g, 0.974 mmol), 2-(tributylstannyl)pyrimidine (0.4 g, 1.07 mmol), CsF (0.3 g, 1.948 mmol), CuI (0.0185 g, 0.098 mmol) and Pd(PPh3)4 (0.112 g, 0.098 mmol) in DMF (5 mL) was degassed and heated at 100° C. oil bath for 16 h. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% EtOAc/hexanes) to yield the title compound as a white solid (0.331 g, 75%). MS (ESI) 459 (M+H).

후처리

  1. customwas degassed
  2. customThe solvent was removed in vacuo
  3. customto obtain the crude which
  4. customwas purified by silica gel chromatography (0˜100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c295d2a9ae1446d8ab9c64665b4f86e3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

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