Cesium carbonate → 3-[[3,5-Difluoro-6-(3-(1-methylimidazolin-2-yl)phenoxy)4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]4-(benzyloxy)benzonitrile

HRID 2299244노트

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HRID 2299244 반응식
[F:1][C:2]1[C:3]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:23]#[N:24])=[N:4][C:5](F)=[C:6]([F:17])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11]1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:42][C:43]1[CH:44]=[C:45]([C:49]2[N:50]([CH3:54])[CH2:51][CH2:52][N:53]=2)[CH:46]=[CH:47][CH:48]=1>CS(C)=O>[F:1][C:2]1[C:3]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:23]#[N:24])=[N:4][C:5]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]3[N:50]([CH3:54])[CH2:51][CH2:52][N:53]=3)[CH:44]=2)=[C:6]([F:17])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 114238803-(1-Methylimidazolin-2-yl)phenolHCID 695506003-[[3,5,6-Trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile

생성물 1

HCID 120165153-[[3,5-Difluoro-6-(3-(1-methylimidazolin-2-yl)phenoxy)4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]4-(benzyloxy)benzonitrile수율 66.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
55 °C

실험 절차

To 3-[[3,5,6-trifluoro-4-[(2,2-dimethyidioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile (1.0 g, 2.1 mmol) in DMSO (6 mL) was added Cs2CO3 (0.7 g, 2.1 mmol) and 2-(3-hydroxyphenyl)-1-methylimidazoline (0.4 g, 2.2 mmol). After stirring in an oil bath at 55° C. for 24 hours, the reaction was partitioned with water and ethyl acetate. The layers were separated, washed with water and brine, dried (Na2SO4), and the solvent was removed in vacuo. The residue was chromatographed on silica with CH2Cl2/MeOH/NH4OH (240/10/1) to give 3-[[3,5-difluoro-6-(3-(1-methylimidazolin-2-yl)phenoxy)-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile (0.9 g).

후처리

  1. customthe reaction was partitioned with water and ethyl acetate
  2. customThe layers were separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica with CH2Cl2/MeOH/NH4OH (240/10/1)

출처 및 근거

ORD 기록
ord-448814b3e561457ea68f520116d274aa
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495684B2

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