Potassium Phosphate, Tribasic → [7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

HRID 626714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626714
Br[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([Cl:19])=[CH:4][N:3]=1.[C:20](=[O:27])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[NH2:21].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:23]([O:22][C:20](=[O:27])[NH:21][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([Cl:19])=[CH:4][N:3]=1)([CH3:26])([CH3:25])[CH3:24]

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 866970524bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 69671401[7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl esterAusbeute 121,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4-bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (400 mg, 1.06 mmol), tert-butyl carbamate (619 mg, 5.3 mmol), Pd2(dba)3 (48 mg, 0.05 mmol), Xantphos (61 mg, 0.1 mmol) and potassium phosphate tribasic (449 mg, 2.1 mmol) in toluene (10 mL) and water (2.0 mL) was purged with argon and heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite® and washed with ethyl acetate. The filtrate was washed with water and brine, dried over sodium sulphate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (531 mg, contaminated with residual tert-butyl carbamate). LCMS (Method D): RT=3.76 min, m/z: 413 [M+H+].

Aufarbeitung

  1. customwas purged with argon
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-7e5aa8b72fd442cb9d42801777fb2e1e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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