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Cesium carbonate → tert-butyl 4-(4-(2-(methylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 522230
ノート
印刷プレビュー

反応式

HRID 522230 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12.[CH3:24][NH:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[CH:28][N:27]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:24][NH:25][C:26]1[C:31]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][C:9]([C:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=4)=[CH:10][C:3]=23)=[CH:30][CH:29]=[CH:28][N:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 72218845N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2-amineHCID 118274390tert-butyl 4-(4-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 118274083tert-butyl 4-(4-(2-(methylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of Example 135D (170 mg, 0.45 mmol), N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (105 mg, 0.45 mmol), bis(triphenylphosphine)palladium(II) chloride (31 mg, 0.045 mmol), tricyclohexylphosphine (13 mg, 0.045 mmol) and cesium carbonate (443 mg, 1.34 mmol) in a round bottom flask was purged with nitrogen. Dioxane (10 mL) was added and the mixture was heated at 100° C. overnight. After cooling, the mixture was triturated with dichloromethane (200 mL) and filtered. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane) to provide the title compound. MS (ESI+) m/z 406 (M+1).

後処理

  1. temperatureAfter cooling
  2. customthe mixture was triturated with dichloromethane (200 mL)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-ffaee0bba07147e3aa9536e63fd3dd65
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328112B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート