Hydrochloric Acid → HCID 76284978, Verbindung

HRID 1778769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778769
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[N:21](C3CCCCO3)[N:20]=[C:19](I)[C:16]2=[N:17][CH:18]=1.[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.C(Cl)(=O)C>O1CCOCC1.O.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[NH:21][N:20]=[C:19]([C:33]3[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=3)[C:16]2=[N:17][CH:18]=1

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86722865HCID 86722865, Verbindung

Produkt 1

HCID 76284978HCID 76284978, VerbindungAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-b]pyridine (25 mg, 0.047 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (12 mg, 0.056 mmol), tetrakis(triphenylphosphine)palladium(0) (3 mg, 0.002 mmol), and cesium carbonate (46 mg, 0.14 mmol) in 1,4-dioxane (0.5 mL) and water (0.07 mL) in a reaction vial was degassed, sealed, and stirred at 85° C. for 3 h. After cooling the mixture was concentrated and the residue was dissolved in methanol (0.4 mL, 10 mmol). To the solution was added HCl solution previously prepared from acetyl chloride (0.3 mL) in methanol (0.3 mL). The mixture was stirred at r.t. for 1 h then concentrated, diluted with methanol, and purified by RP-HPLC (pH=2) to afford the desired product (3.9 mg) as a TFA salt. LCMS (M+H)+=404.1.

Aufarbeitung

  1. customin a reaction
  2. customvial was degassed
  3. customsealed
  4. temperatureAfter cooling the mixture
  5. concentrationwas concentrated
  6. stirringThe mixture was stirred at r.t. for 1 h
  7. concentrationthen concentrated
  8. additiondiluted with methanol
  9. custompurified by RP-HPLC (pH=2)

Quellen und Nachweise

ORD-Eintrag
ord-352e8a6c4178457794ddb81fc7d4ddf8
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266892B2

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