5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one → 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 577602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577602
[NH2:1][C:2]1[C:11](I)=[C:10]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][C:14]=2[CH3:19])[C:9]([Cl:20])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:21]>[Pd].C(O)(=O)C.CO>[NH2:1][C:2]1[CH:11]=[C:10]([C:13]2[N:17]([CH3:18])[N:16]=[N:15][C:14]=2[CH3:19])[C:9]([Cl:20])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:21]

Komponenten

5

Edukt 1

HCID 867238285-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one

Produkt 1

HCID 867238295-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 178,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

Two batches were prepared by the following method: a mixture of 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one (293f, 2.9 g, 6.9 mmol each batch) and palladium on carbon (2.9 g) in glacial acetic acid (29 mL) and methanol (290 mL) was stirred under a hydrogen balloon at room temperature overnight. The combined reaction mixtures were filtered through celite, and the filter pad washed with methanol (300 mL). The filtrate was concentrated and the residue purified by silica gel chromatography (eluting with 10:1 dichloromethane/methanol) affording 5-amino-8-chloro-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (293g, 3.6 g, 65% combined yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 6.82 (s, 1H), 3.75 (s, 3H), 3.29-3.28 (m, 2H), 2.70-2.67 (m, 2H), 2.07 (s, 3H). MS: 292 [M+1].

Aufarbeitung

  1. customTwo batches were prepared by the following method
  2. customThe combined reaction mixtures
  3. filtrationwere filtered through celite
  4. washthe filter pad washed with methanol (300 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified by silica gel chromatography (eluting with 10:1 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-52348bbc034c448696541b48f736140b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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