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2-Methoxypyrimidine-5-boronic acid → 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxypyrimidin-5-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide

HRID 1442832
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1442832
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][N:4]=1.Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]([C:22]2([C:25]3[CH:35]=[CH:34][C:28]4[O:29][C:30]([F:33])([F:32])[O:31][C:27]=4[CH:26]=3)[CH2:24][CH2:23]2)=[O:21])[CH:16]=[CH:15][C:14]=1[CH3:36]>COCCOC.C([O-])([O-])=O.[Na+].[Na+].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>[F:33][C:30]1([F:32])[O:29][C:28]2[CH:34]=[CH:35][C:25]([C:22]3([C:20]([NH:19][C:17]4[CH:16]=[CH:15][C:14]([CH3:36])=[C:13]([C:6]5[CH:5]=[N:4][C:3]([O:2][CH3:1])=[N:8][CH:7]=5)[N:18]=4)=[O:21])[CH2:24][CH2:23]3)=[CH:26][C:27]=2[O:31]1
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Komponenten

6

Edukt 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 59165796N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide

Produkt 1

HCID 591658501-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxypyrimidin-5-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a mixture of 2-methoxypyrimidin-5-ylboronic acid (92 mg, 0.60 mmol) and N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamide (180 mg, 0.50 mmol) in DME (3 mL) and 2 M Na2CO3 (1 mL) was added Pd(PPh3)4 (29 mg, 0.025 mmol). The mixture was heated in a microwave oven at 120° C. for 30 min. The mixture was partitioned between ethyl acetate and H2O and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxypyrimidin-5-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide (140 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 2H), 8.03 (d, J=8.4 Hz, 1H), 7.58 (s, 1H), 7.53 (d, J=8.5 Hz, 1H), 7.18 (dd, J=8.6, 2.1 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 7.04 (d, J=8.2 Hz, 1H), 3.98 (s, 3H), 2.26 (s, 3H), 1.68 (q, J=3.6 Hz, 2H), 1.12 (q, J=3.6 Hz, 2H). MS (ESI) m/e (M+H+) 441.3.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and H2O
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8c88e46b968d439b931cc8cf275cd6fb
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07659268B2

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