Potassium Carbonate → (2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid methyl ester

HRID 1485932

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=1)[CH3:13].Br[C:34]1[C:35]([CH3:41])=[CH:36][C:37]([Cl:40])=[N:38][CH:39]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:34]2[CH:39]=[N:38][C:37]([Cl:40])=[CH:36][C:35]=2[CH3:41])[CH:16]=1)[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A mixture of (2-{[4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid methyl ester (45 mg, 0.11 mmol), 5-bromo-2-chloro-4-methyl-pyridine (25 mg, 0.12 mmol), Pd(PPh3)4 (6.5 mg, 0.0056 mmol), and K2CO3 (38 mg, 0.28 mmol) in dioxane (600 ul), was heated at 95° C. for 12 hrs. The mixture was purified after a filtration by prep. LCMS to yield (2-{[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid methyl ester 3-1. MS [M+H]+: 459.0; tR=7.70 min; (method 2)

Aufarbeitung

customThe mixture was purified
filtrationafter a filtration by prep

Quellen und Nachweise

ORD-Eintrag: ord-d48b59bee2e74c3d9348eb13ced36fe4
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09422310B2

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