Potassium Carbonate → Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl ester

HRID 1671800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671800
Cl[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[S:10][C:4]=2[CH:3]=1.[C:15]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([O-:47])([O-])=[O:45].[K+].[K+]>CO.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]([NH:11][C:9]1[S:10][C:4]2[CH:3]=[C:2]([C:44]([O:47][CH3:15])=[O:45])[N:7]=[CH:6][C:5]=2[N:8]=1)([CH3:14])[CH3:13]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 575272276-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine

Produkt 1

HCID 57527243Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl esterAusbeute 301,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine (0.24 g, 1.05 mmol, 1.0 eq.), Pd(OAc)2 (0.0313 g, 0.139 mmol, 0.1 eq.), 1,3-bis(diphenylphosphino)propane (0.0443 g, 0.107 mmol, 0.1 eq.) and K2CO3 (0.2214 g, 1.60 mmol, 1.5 eq.) in MeOH (2.6 mL) and DMF (1.3 mL) was stirred under an atmosphere of CO inside a bomb (40 psi) at 91° C. overnight. After cooling to room temperature, the reaction mixture was filtered through Celite and rinsed with MeOH. The filtrate was concentrated in vacuo, diluted with EtOAc and water. The layers were separated, and the organic layer was washed with brine and 10% aqueous LiCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2:MeOH (10:0.3) to give methyl 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carboxylate as a white solid (0.081 g, 31% yield).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through Celite
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with EtOAc and water
  5. customThe layers were separated
  6. washthe organic layer was washed with brine and 10% aqueous LiCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with CH2Cl2:MeOH (10:0.3)

Quellen und Nachweise

ORD-Eintrag
ord-a97e5ef1858d4193802d911fd0be2f94
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994337B2

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