Potassium Phosphate, Tribasic → HCID 67173284, 화합물

HRID 1891271노트

반응식

HRID 1891271 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 67173284HCID 67173284, 화합물수율 54.7%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4e87aa69028842548b93bd19280714cc
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507521B2

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