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Potassium Phosphate, Tribasic → HCID 71767099, Verbindung

HRID 516973
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 516973
Cl[C:2]1[CH:11]=[C:10]([C:12]([NH:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][CH:31]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.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>[O:40]1[CH2:41][CH2:42][N:37]([CH2:36][C:33]2[CH:32]=[CH:31][C:30]([C:2]3[CH:11]=[C:10]([C:12]([NH:14][CH2:15][CH2:16][N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)=[O:13])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)=[CH:35][CH:34]=2)[CH2:38][CH2:39]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterHCID 606827052-chloro-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide

Produkt 1

HCID 71767099HCID 71767099, VerbindungAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a sealed 5 ml microwave tubed, a suspension of 2-chloro-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide (preparation 11) (200 mg, 0.66 mmol), 4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]morpholine (preparation 2) (399 mg, 1.31 mmol), potassium phosphate (419 mg, 1.97 mmol) and tetrakis(triphenylphosphine)palladium (0) (22 mg, 0.02 mmol) in DMF/Water 3/1 (4 ml) was heated at 130° C. under microwave irradiation for 30 minutes. The reaction was filtered through Celite™ and solvents were removed under reduced pressure. The resulting residue was taken up in DCM (50 ml) and washed with NaHCO3 saturated aqueous solution (25 ml). The organic layer was separated and dried over MgSO4 before concentration to dryness. The reaction crude was purified by preparative HPLC. The fractions containing product were pooled together and freeze dried to obtain the desired compound as a white solid (220 mg, 0.49 mmol, Yield 57%).

Aufarbeitung

  1. filtrationThe reaction was filtered through Celite™ and solvents
  2. customwere removed under reduced pressure
  3. washwashed with NaHCO3 saturated aqueous solution (25 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4 before concentration to dryness
  6. customThe reaction crude
  7. customwas purified by preparative HPLC
  8. additionThe fractions containing product
  9. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-87fc248d19d045c5ab9a7f2a19f1c7aa
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115088B2

Notizen zur Reaktion

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