Bromine → (R,R)-N-[4-bromo-3-(3-fluoro-4-methoxyphenyl)-isothiazol-5-yl]-2-methylcyclopropanecarboxamide

HRID 2422714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422714
[Br:1]Br.[F:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:16]=[C:15]([NH:17][C:18]([C@@H:20]3[CH2:22][C@H:21]3[CH3:23])=[O:19])[S:14][N:13]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl.CCOC(C)=O>[Br:1][C:16]1[C:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([F:3])[CH:5]=2)=[N:13][S:14][C:15]=1[NH:17][C:18]([C@@H:20]1[CH2:22][C@H:21]1[CH3:23])=[O:19]

Komponenten

6

Edukt 3

HCID 24408Bromine2×HCID 24477Sodium ThiosulfateHCID 67180639(R,R)-N-[3-(3-fluoro-4-methoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide

Produkt 1

HCID 67180682(R,R)-N-[4-bromo-3-(3-fluoro-4-methoxyphenyl)-isothiazol-5-yl]-2-methylcyclopropanecarboxamideAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add bromine (0.15 mL, 0.47 g, 2.94 mmol) to (R,R)—N-[3-(3-fluoro-4-methoxy-phenyl)isothiazol-5-yl]-2-methylcyclopropanecarboxamide (0.45 g, 1.47 mmol) in dichloromethane (3 mL) dropwise. Monitor by TLC and stop bromine addition when complete. Dilute the reaction mixture with EtOAc (100 mL) and pour into aqueous Na2S2O3 (1 N). Collect the organic phase, wash with brine (50 mL) and water (80 mL), and evaporate. Chromatograph over silica gel, eluting with 10-50% EtOAc in hexane, to afford (R,R)—N-[4-bromo-3-(3-fluoro-4-methoxyphenyl)isothiazol-5-yl]-2-methyl-cyclopropanecarboxamide. Yield: 97.1%. ES-MS: m/e 387.0 (m+1).

Aufarbeitung

  1. customCollect the organic phase
  2. washwash with brine (50 mL) and water (80 mL)
  3. customevaporate
  4. washChromatograph over silica gel, eluting with 10-50% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ad2abfaa1a08485997f2916722a1b490
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960419B2

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