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Cesium carbonate → 5-((R)-1-(3,5-Dichloropyridin-4-yl)ethoxy)-1-(tetrahydro-2H-pyran-2-yl)-3-((E)-2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazole

HRID 2387420
ノート
印刷プレビュー

反応式

HRID 2387420 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[C:9](/[CH:17]=[CH:18]/[C:19]2[CH:20]=[N:21][N:22]([CH2:24][CH2:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[CH:23]=2)=[N:8]1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[C@H:44]([C:46]1[C:51]([Cl:52])=[CH:50][N:49]=[CH:48][C:47]=1[Cl:53])[CH3:45])(=O)=O>C(#N)C>[Cl:53][C:47]1[CH:48]=[N:49][CH:50]=[C:51]([Cl:52])[C:46]=1[C@H:44]([O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[N:8]=[C:9]2/[CH:17]=[CH:18]/[C:19]1[CH:20]=[N:21][N:22]([CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:23]=1)[CH3:45]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 66831604(E)-1-(Tetrahydro-2H-pyran-2-yl)-3-(2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazol-5-olHCID 86647459(S)-1-(3,5-Dichloropyridin-4-yl)ethyl methanesulfonate

生成物 1

HCID 666468355-((R)-1-(3,5-Dichloropyridin-4-yl)ethoxy)-1-(tetrahydro-2H-pyran-2-yl)-3-((E)-2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

In a 3-neck 250 mL round bottom flask equipped with an internal temperature probe, reflux condenser, nitrogen blanket and magnetic stir bar, slurry (E)-1-(tetrahydro-2H-pyran-2-yl)-3-(2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazol-5-ol (10.0 g, 22.83 mmol) and cesium carbonate (7.88 g, 23.94 mmol) in ACN (92 mL) and warm to 60° C. To the suspension, add (S)-1-(3,5-dichloropyridin-4-yl)ethyl methanesulfonate (7.03 g, 26.02 mmol) and stir overnight. Cool the reaction mixture to RT, filter and wash solids with ACN. Concentrate the filtrate and purify the residue by silica gel chromatography (2-4% (2 M ammonia in methanol)/DCM). Combine product fractions and concentrate in vacuo to a white foam. Yield: 12.5 g (86%). MS (ES) m/z 612 [M+1]+.

後処理

  1. customIn a 3-neck 250 mL round bottom flask equipped with an internal temperature probe
  2. temperaturereflux condenser
  3. filtrationfilter
  4. washwash solids with ACN
  5. concentrationConcentrate the filtrate
  6. custompurify the residue by silica gel chromatography (2-4% (2 M ammonia in methanol)/DCM)
  7. concentrationCombine product fractions and concentrate in vacuo to a white foam

出典と根拠

ORDレコード
ord-30b342168a0f45e7875f9ae46c106284
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08268869B2

反応ノート

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