Hydrochloric Acid → Methyl 3-aminoisoquinoline-8-carboxylate

HRID 920254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920254
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([O:14][CH3:15])=[O:13].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[Li+].C[Si]([N-:46][Si](C)(C)C)(C)C.Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[NH2:46][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([O:14][CH3:15])=[O:13]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 89524931Methyl 3-chloroisoquinoline-8-carboxylate

Produkt 1

HCID 89524691Methyl 3-aminoisoquinoline-8-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A 20 mL microwave vial was charged with methyl 3-chloroisoquinoline-8-carboxylate (0.56 g, 2.57 mmol), [1,1′-biphenyl]-2-yldicyclohexylphosphine (90 mg, 0.257 mmol), LHMDS (3.0 mL, 3.08 mmol) and Pd2(dba)3 (118 mg, 0.125 mmol) and then with 12 mL of THF. Reaction mixture was capped and stirred at 65° C. overnight. Then 2M HCl (1.2 mL, 2.57 mmol) was added and stirred at rt for 20 min. The reaction mixture was filtered and added with sat bi carb. Extracted with EtOAc. Combined organic layer was dried, filtered, concentrated in vacuo. Purified by silica gel chromatography (0-50% EtOAc in hexane) yielded 90% Methyl 3-aminoisoquinoline-8-carboxylate (27-2).

Aufarbeitung

  1. customReaction mixture
  2. customwas capped
  3. stirringstirred at rt for 20 min
  4. filtrationThe reaction mixture was filtered
  5. additionadded
  6. extractionExtracted with EtOAc
  7. customCombined organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurified by silica gel chromatography (0-50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bcafa59648824708b402f5d27ff68b42
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273040B2

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