Sodium borohydride → 3-Fluoro-4-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-thieno[3,2-b]pyridin-7-yloxy]-phenylamine

HRID 2193680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193680
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)[S:13][C:6]=12.[BH4-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:18][CH:19]=3)[S:13][C:6]=12

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 58790077HCID 58790077, Verbindung

Produkt 1

HCID 587903253-Fluoro-4-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-thieno[3,2-b]pyridin-7-yloxy]-phenylamineAusbeute 108,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the nitro compound 53 (256 mg, 0.57 mmol) in a mixture of MeOH (12 mL) and THF (4 mL) at 0° C. was added NiCl2.6H2O (279 mg, 1.14 mmol), followed by portion wise addition of NaBH4 (87 mg, 2.27 mmol). The reaction mixture turned black after 15 min, and was filtered through a celite pad; the filtrate concentrated under reduced pressure. The residue was suspended in 2N HCl and the solids were removed by filteration. The filtrate was basified with NH4OH to pH˜10 then extracted with EtOAc. The organic phase was concentrated to afford the title compound 54 (260 mg, crude, >100% yield, HPLC pure) as yellowish foam. MS (m/z): 420.1 (M+H).

Aufarbeitung

  1. filtrationwas filtered through a celite pad
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe solids were removed by filteration
  4. extractionthen extracted with EtOAc
  5. concentrationThe organic phase was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bf7ec401e41e4c768abf64d130efb2d0
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329726B2

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