Hydrochloric Acid → HCID 58011821, Verbindung

HRID 660882Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:7](Br)=[N:6]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[C:24]([O:31][CH3:32])[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>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>[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:7]([C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][C:24]=2[O:31][CH3:32])=[N:6]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Under argon, 250 mg (0.73 mmol) of the compound from Example 146A and 190 mg (1.07 mmol) of 4-chloro-2-methoxyphenylboronic acid are dissolved in 7 ml degassed DMF. A previously degassed solution of sodium carbonate (2 N in water, 1.09 ml, 2.18 mmol) and 42 mg of tetrakis(triphenylphosphine)palladium (0.036 mmol) are added. The resulting mixture is heated and stirred for 8 hrs at 90° C. After cooling to RT it is acidified with 10% hydrochloric acid and the mixture filtered. The filtrate is purified by preparative HPLC (Method 20). 159 mg (54% of theory) of the title compound and 54 mg (18% of theory) of the corresponding acid formed by hydrolysis (see also Example 148A) are obtained.

Aufarbeitung

customdegassed DMF
temperatureThe resulting mixture is heated
temperatureAfter cooling to RT it
filtrationthe mixture filtered
customThe filtrate is purified by preparative HPLC (Method 20)

Quellen und Nachweise

ORD-Eintrag: ord-d52fe195bdb241f4b0f9df181d8252d5
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08084481B2

Notizen zur Reaktion

Wird geladen…