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Potassium Phosphate, Tribasic → 3-(4-(2-Cyclopropyl-1-oxoisoindolin-5-yl)benzyl)-1-methylimidazoline-2,4-dione

HRID 1891261
ノート
印刷プレビュー

反応式

HRID 1891261 の反応式
[CH:1]1([N:4]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9](B4OC(C)(C)C(C)(C)O4)[CH:10]=3)[C:5]2=[O:22])[CH2:3][CH2:2]1.Br[C:24]1[CH:38]=[CH:37][C:27]([CH2:28][N:29]2[C:33](=[O:34])[CH2:32][N:31]([CH3:35])[C:30]2=[O:36])=[CH:26][CH:25]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(Cl)Cl.O>[CH:1]1([N:4]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:24]4[CH:38]=[CH:37][C:27]([CH2:28][N:29]5[C:33](=[O:34])[CH2:32][N:31]([CH3:35])[C:30]5=[O:36])=[CH:26][CH:25]=4)[CH:10]=3)[C:5]2=[O:22])[CH2:2][CH2:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 594023502-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 606247733-[(4-Bromophenyl)methyl]-1-methylimidazolidine-2,4-dione

生成物 1

HCID 529318563-(4-(2-Cyclopropyl-1-oxoisoindolin-5-yl)benzyl)-1-methylimidazoline-2,4-dione収率 2,280.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (1A5) (0.08 mmol, 26.4 mg), 3-(4-bromobenzyl)-1-methylimidazolidine-2,4-dione (3D3) (0.08 mmol, 25.0 mg), tris(dibenzylidineacetone)dipalladium (0.004 mmol, 4.12 mg), tricyclohexylphosphine (0.096 mmol, 3.1 mg) and potassium phosphate (0.16 mmol, 39.0 mg) were suspended in dioxane (1 ml) and water (0.5 ml) and heated at 120° C. in the microwave for 20 min. The reaction was diluted with DCM (2 ml) and water (2 ml) then passed through a hydrophobic fritted tube. The organic phase was concentrated and the residue purified on basic HPLC to give 3-(4-(2-cyclopropyl-1-oxoisoindolin-5-yl)benzyl)-1-methylimidazoline-2,4-dione (Example 3a) (685 mg, 55%) 1H NMR (400 MHz, CDCl3) δ 7.87 (d, 1H) 7.64 (d, 1H) 7.57-7.50 (m, 5H) 4.71 (s, 2H) 4.37 (s, 2H) 3.89 (s, 2H) 3.01 (s, 3H) 2.95 (m, 1H) 0.95-0.88 (m, 4H) LCMS m/z (M+H) 376.0.

後処理

  1. customthen passed through a hydrophobic fritted tube
  2. concentrationThe organic phase was concentrated
  3. customthe residue purified on basic HPLC

出典と根拠

ORDレコード
ord-c494d3ee8ff4460992b26095e9dfa701
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507521B2

反応ノート

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