Water → 4-(3-Carbamoylphenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21212

Reaktionsgleichung

Reaktionsgleichung von HRID 21212
FC(F)(F)S(O[C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39])(=O)=O.[NH2:42][C:43]([C:45]1[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][CH:50]=1)=[O:44].C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[C:43]([C:45]1[CH:50]=[C:49]([C:7]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:18]4[C:23]([CH:24]=3)=[CH:22][C:21]([CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)=[CH:20][CH:19]=4)=[C:12]3[C:8]=2[CH2:9][NH:10][C:11]3=[O:39])[CH:48]=[CH:47][CH:46]=1)(=[O:44])[NH2:42]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 866282864-Trifluoromethanesulfonyloxy-7-(1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Produkt 1

HCID 684936044-(3-Carbamoylphenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (80.0 mg, 0.135 mmol) was dissolved in dimethoxyethane (5.6 mL), and the solution was added with (3-aminocarbonylphenyl)boronic acid (89 mg, 0.54 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (17.6 mg, 0.0216 mmol), potassium carbonate (93.0 mg, 0.675 mmol) and water (0.049 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1) to obtain 4-(3-carbamoylphenyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (36.1 mg, yield 47%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-845493a3fd3f471ba8971f7784e37816
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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