Sodium borohydride → N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 84706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84706
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:27])[C:10]([C:12]1[S:24][C:23]2[C:22]3[CH:21]=[C:20]([CH:25]=[O:26])[CH:19]=[CH:18][C:17]=3[O:16][CH2:15][C:14]=2[CH:13]=1)=[O:11].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:27])[C:10]([C:12]1[S:24][C:23]2[C:22]3[CH:21]=[C:20]([CH2:25][OH:26])[CH:19]=[CH:18][C:17]=3[O:16][CH2:15][C:14]=2[CH:13]=1)=[O:11]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 57900416N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Produkt 1

HCID 57900161N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide in ethanol (1 mL) was added sodium borohydride (10 mg, 0.3 mmol, 6 equiv). After 3 hr, excess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL). The ethanol was removed in vacuo, and the resulting aqueous solution was extracted with ethylacetate (3×3 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (3:2 hexanes/ethylacetate) provided 159bp (5.2 mg, 30%). 1H NMR (500 MHz, CDCl3) δ 7.26 (m, 1 H), 7.15 (m, 1 H), 7.05 (m, 1 H), 6.86-6.93 (m, 4 H,), 5.25 (s, 2 H), 4.55 (d, J=6.7 Hz, 2 H), 4.06 (m, 1 H), 3.40 (s, 3 H). LCMS (ESI) m/z: 388.1.

Aufarbeitung

  1. customexcess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL)
  2. customThe ethanol was removed in vacuo
  3. extractionthe resulting aqueous solution was extracted with ethylacetate (3×3 mL)
  4. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (3:2 hexanes/ethylacetate)
  8. customprovided 159bp (5.2 mg, 30%)

Quellen und Nachweise

ORD-Eintrag
ord-942eda8fef744b2d8439399fd36c74c8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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