Dichloromethane → HCID 178492096, Verbindung

HRID 2388987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388987
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:9][N:8](COC(=O)C(C)(C)C)[C:5]2=[N:6][CH:7]=1.[NH2:27][C:28]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][C:29]=1[C:30]([N:32]([CH3:34])[CH3:33])=[O:31].ClCCl.C(=O)(O)[O-].[Na+]>O1CCCC1.C(#N)C.O>[NH2:27][C:28]1[CH:38]=[CH:37][C:36]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=4)=[N:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:35][C:29]=1[C:30]([N:32]([CH3:34])[CH3:33])=[O:31]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 574162382-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 686631372,2-Dimethyl-propionic acid 5-bromo-3-(3-methoxy-pyridin-2-yl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester

Produkt 1

HCID 178492096HCID 178492096, VerbindungAusbeute 38,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,2-Dimethyl-propionic acid 5-bromo-3-(3-methoxy-pyridin-2-yl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (570 mg, 1.36 mmol), 2-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (570 mg, 1.96 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex in dichloromethane (1:1, 111 mg, 0.136 mmol), tetrahydrofuran (3 ml), acetonitrile (6 ml), water (3 ml), and saturated sodium bicarbonate (3 ml) were combined and irradiated in a microwave reactor for 20 minutes at 120° C. Water was added to the reaction mixture, and this was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes) to give 205 mg (31%) 2-amino-5-[3-(3-methoxy-pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide. MS: m/z 503.4 (M+H+).

Aufarbeitung

  1. customirradiated in a microwave reactor for 20 minutes at 120° C
  2. extractionthis was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-661d2f9a80f842a98c344a6f14262f53
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268994B2

Notizen zur Reaktion

Wird geladen…