Triethylamine → N-(6-Bromo-5-methoxypyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 2420894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2420894
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].CCN(CC)CC.[F:18][C:19]1([F:34])[O:23][C:22]2[CH:24]=[CH:25][C:26]([C:28]3([C:31](Cl)=[O:32])[CH2:30][CH2:29]3)=[CH:27][C:21]=2[O:20]1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:31]([C:28]2([C:26]3[CH:25]=[CH:24][C:22]4[O:23][C:19]([F:34])([F:18])[O:20][C:21]=4[CH:27]=3)[CH2:30][CH2:29]2)=[O:32])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 127582096-Bromo-5-methoxypyridin-2-amineHCID 575168501-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chloride

Produkt 1

HCID 59165869N-(6-Bromo-5-methoxypyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 6-bromo-5-methoxypyridin-2-amine (510 mg, 2.5 mmol) and Et3N (690 □L, 4.9 mmol) in dichloromethane (10 mL) was added a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (650 mg, 2.5 mmol) in dichloromethane (5 mL). The resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was then washed with 1N HCl (1×20 mL) and saturated aqueous NaHCO3 (1×20 mL). The organics were dried over sodium sulfate and evaporated to yield the product (850 mg, 81%). ESI-MS m/z calc. 426.0, found 427.3 (M+1)+. Retention time 2.05 minutes.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe reaction mixture was then washed with 1N HCl (1×20 mL) and saturated aqueous NaHCO3 (1×20 mL)
  3. dry with materialThe organics were dried over sodium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-09e874fc59854482b89d07ca5fb40198
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956052B2

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