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Sodium Carbonate → 2-(1H-indol-5-yl)-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide

HRID 2410902
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2410902
Br[C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[NH:39][CH:38]=[CH:37]3)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C([O-])([O-])=O.[Na+].[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C1(C)C=CC=CC=1.C1COCC1>[NH:39]1[C:40]2[C:36](=[CH:35][C:34]([C:2]3[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]4[NH:6][C:7]5[CH:8]=[C:9]([C:15]([N:17]6[CH2:18][CH2:19][O:20][CH2:21][CH2:22]6)=[O:16])[CH:10]=[CH:11][C:12]=5[C:13]=4[N:14]=3)=[CH:42][CH:41]=2)[CH:37]=[CH:38]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 5

HCID 10340Sodium CarbonateHCID 62657Potassium Phosphate, TribasicHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 866630712-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide

Produkt 1

HCID 66604688
2-(1H-indol-5-yl)-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2-Bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide (60 mg, 0.149 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (72.3 mg, 0.298 mmol), Potassium phosphate tribasic (134 mg, 0.476 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (24.43 mg, 0.060 mmol) and Pd(OAc)2 (6.68 mg, 0.030 mmol) were mixed with THF (2 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 85° C. in an oil bath for 3.5 hr. LC/MS showed there was trace amount of product formed. The reaction mixture was blown to dryness under N2 blower. To the mixture was added Pd(Ph3P)4 (34.4 mg, 0.030 mmol), Toluene (3 mL), MeOH (1.5 mL) and Na2CO3 (2M) (0.149 mL, 0.298 mmol). The mixture was then heated at 100° C. for 3 hrs. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 440.3 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.65 (s, 1H), 11.20 (s, 1H), 8.67 (s, 1H), 8.5 (m, 2H), 8.32 (d, 1H, J=8.2), 8.12 (d, 1H, J=8.5), 7.9 (s, 1H), 7.8 (s, 1H), 7.53(d, 1H, J=8.0), 7.41(m, 1H), 7.30 (d, 1H, J=8.0), 6.57 (s, 1H), 3.66 (bs, 8H).

Aufarbeitung

  1. customThe mixture was flushed with N2
  2. customformed
  3. temperatureThe mixture was then heated at 100° C. for 3 hrs
  4. concentrationThe mixture was concentrated
  5. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-6557ff14ff61491aaf6560c99c62f6be
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815840B2

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