3-Amino-5-cyanobenzeneboronic acid hydrochloride → 3-Amino-5-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydrospiro [chroman-4,4'-imidazole]-6-yl)benzonitrile

HRID 2096405

Reaktionsgleichung

Reaktionsgleichung von HRID 2096405
[NH2:1][C:2]1[N:3]([CH2:24]C2CCCCC2)[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.Cl.[NH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([C:39]#[N:40])[CH:38]=1>O1CCOCC1.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>[NH2:32][C:33]1[CH:38]=[C:37]([CH:36]=[C:35]([C:13]2[CH:14]=[C:15]3[C:5]4([C:4](=[O:23])[N:3]([CH3:24])[C:2]([NH2:1])=[N:6]4)[CH2:7][CH:8]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[O:9][C:10]3=[CH:11][CH:12]=2)[CH:34]=1)[C:39]#[N:40]

Komponenten

6

Edukt 2

HCID 441193543-Amino-5-cyanobenzeneboronic acid hydrochlorideHCID 584244092'-amino-6-bromo-1'-(cyclohexylmethyl)-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one

Produkt 1

HCID 584245123-Amino-5-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydrospiro [chroman-4,4'-imidazole]-6-yl)benzonitrileAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 10796Cesium carbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Pd(PPh3)2Cl2 (10 mg) in a 10 mL tube under Ar was treated sequentially with 2′-amino-6-bromo-1′-(cyclohexylmethyl)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.052 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 N, 0.3 mL) and 3-amino-5-cyanophenylboronic acid hydrochloride (21 mg, 0.104 mmol). The mixture was heated at 120° C. under microwave reactor for 0.5 h. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC followed by preparative HPLC to give pure 3-amino-5-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro [chroman-4,4′-imidazole]-6-yl)benzonitrile (3.53 mg, 16%). 1H-NMR (MeOD): 2.44 (m, 1H), 2.60 (m, 1H), 5.24 (d, 0.3H), 5.85 (d, 0.7H), 6.91 (m, 1H), 7.14 (m, 3H), 7.48 (m, 6H), 7.60 (m, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the residue, which
  3. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-feb8f60fc6e24ad08ac12b5db77eeb69
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450308B2

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