Sodium hydride → (3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-carbamic acid tert-butyl ester

HRID 57149

Reaktionsgleichung

Reaktionsgleichung von HRID 57149
[H-].[Na+].[C:3]([O:7][C:8](=[O:20])[NH:9][C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]=1[CH3:19])([CH3:6])([CH3:5])[CH3:4].[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:25]Br>CN(C=O)C.O>[C:3]([O:7][C:8](=[O:20])[N:9]([CH2:25][C:24]1[CH:27]=[CH:28][C:29]([F:30])=[C:22]([F:21])[CH:23]=1)[C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]=1[CH3:19])([CH3:6])([CH3:5])[CH3:4]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 57920379Tert-butyl-3-methylbenzo[b]thiophen-2-ylcarbamate

Produkt 1

HCID 57920462(3,4-Difluoro-benzyl)-(3-methyl-benzo[b]thiophen-2-yl)-carbamic acid tert-butyl esterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60%, 0.37 g, 9.19 mmol) was added to a solution of compound 125-B (2.2 g, 8.35 mmol) in DMF (30 mL), at 0° C. and the resultant mixture was stirred for 15 minutes. 3,4-Difluorobenzylbromide (1.18 mL, 9.2 mmol) was added, and the solution was stirred at ambient temperature for 2 h. The reaction mixture was diluted with water, extracted with ethyl acetate, the organic extract washed with water (3×), brine, dried over sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude residue was purified by flash column chromatography, eluting with an ethyl acetate-heptane gradient, to afford compound 125-C as an oil (2.73 g, 84%). 1H-NMR (CDCl3): δ 1.40 (s, 9H), 1.97 (s, 3H), 4.72 (s, 2H), 6.93-7.19 (m, 3H), 7.28-7.39 (m, 2H), 7.61 (d, 1H), 7.70 (d, 1H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionthe organic extract
  3. washwashed with water (3×), brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe crude residue was purified by flash column chromatography
  8. washeluting with an ethyl acetate-heptane gradient

Quellen und Nachweise

ORD-Eintrag
ord-635519949ce64f238a8520d82754a5f1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434711B2

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