Potassium Phosphate, Tribasic → HCID 67173284、化合物

HRID 1891271ノート

反応式

HRID 1891271 の反応式
Br[C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:11]([CH3:13])([CH3:12])[C:10](=[O:14])[NH:9][C:8]2=[O:15])=[CH:4][CH:3]=1.BrC1C=CC(CN2CC(=O)NC2=O)=CC=1.[CH:33]1([N:36]2[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[C:41](B4OC(C)(C)C(C)(C)O4)[CH:42]=3)[C:37]2=[O:54])[CH2:35][CH2:34]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[CH:33]1([N:36]2[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[C:41]([C:2]4[CH:17]=[CH:16][C:5]([CH2:6][N:7]5[C:11]([CH3:13])([CH3:12])[C:10](=[O:14])[NH:9][C:8]5=[O:15])=[CH:4][CH:3]=4)[CH:42]=3)[C:37]2=[O:54])[CH2:35][CH2:34]1

参加物

8

反応物 5

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 154067221-(4-Bromobenzyl)imidazolidine-2,4-dioneHCID 594023502-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 64217701HCID 64217701、化合物

生成物 1

HCID 67173284HCID 67173284、化合物収率 54.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

1-(4-bromobenzyl)-5,5-dimethylimidazolidine-2,4-dione (8B4) (0.168 mmol, 50 mg) (prepared according to the method described for intermediate (1B4), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (1A5) (0.1 mmol, 53.0 mg), tris(dibenzylidineacetone)dipalladium (0.008 mmol, 8.1 mg), tricyclohexylphosphine (0.02 mmol, 5.7 mg) and potassium phosphate (0.27 mmol, 60.7 mg) were suspended in dioxane (3 ml) and water (1 ml) and heated to 130° C. in the microwave for 15 min. The reaction mixture was quenched with water (6 ml) and DCM (9 ml) and the organic layer separated using a hydrophobic fritted tube. The organic phase was concentrated and the residue purified on silica eluting with 0-100% EtOAc/heptane to give 1-(4-(2-cyclopropyl-1-oxoisoindolin-5-yl)benzyl)-5,5-dimethylimidazolidine-2,4-dione (8I1) 21.3 mg (53%); 1H NMR (400 MHz, CDCl3) δ 7.88 (d, 1H) 7.54 (d, 1H) 7.57 (m, 3H) 7.43 (d, 2H) 7.33 (bs, 1H) 4.56 (s, 2H) 4.37 (s, 2H) 3.94 (m, 1H) 1.34 (s, 6H) 0.95-0.88 (m, 4H).

後処理

  1. customThe reaction mixture was quenched with water (6 ml) and DCM (9 ml)
  2. customthe organic layer separated
  3. concentrationThe organic phase was concentrated
  4. customthe residue purified on silica eluting with 0-100% EtOAc/heptane

出典と根拠

ORDレコード
ord-4e87aa69028842548b93bd19280714cc
出典データセット
uspto-grants-2013_08
特許番号
US08507521B2

反応ノート

読み込み中…