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 1267091ノート

反応式

HRID 1267091 の反応式
[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

参加物

5

反応物 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

生成物 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)benzonitrile収率 66.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
55 °C

実験手順

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-dimethyidioxolan-4-yl)methoxylpyridin-2-yl]oxy]4-(benzyloxy)benzonitrile (0.9 g).

後処理

  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)

出典と根拠

ORDレコード
ord-c6d8fb33e6dd4d0098dfe232802b623f
出典データセット
uspto-grants-2003_04
特許番号
US06552030B2

反応ノート

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