Sodium methanethiolate → 4-(3-Methylsulfanyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 68749

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18](I)=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S-:25].[Na+].CC(C)([O-])C.[Na+].C1(P(C(C)(C)C)F)CCCCC1>COCCOC.CCCCCCC.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([S:25][CH3:24])=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 4-(3-iodo-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (213 mg, 0.50 mmol), sodium methanethiolate (39 mg, 0.55 mmol) and sodium tert-butoxide (67 mg, 0.7 mmol) in a pre-dried flask sealed under N2 was added 1 mL of a catalyst solution, which was prepared by mixing Pd(OAc)2 (12.4 mg, 0.055 mml) and JOSIPHOS CyPF-t-Bu (30.6 mg, 0.055 mmol) in DME (1.1 mL) under N2. The resulting mixture was heated in 100° C. oil bath for 5 h, then cooled and loaded onto a silica-gel column and chromatography (gradient eluant 20% to 50% EtOAc in heptane) to yield 4-(3-Methylsulfanyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as white crystalline solid.

Aufarbeitung

customsealed under N2
customwas prepared
temperaturecooled

Quellen und Nachweise

ORD-Eintrag: ord-973c579cd9854cb681b6e04dc8643d49
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822447B2

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