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Triethylamine → 6-Bromo-2-(1-(difluoromethyl)-1H-pyrazol-4-yl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridine

HRID 2205946
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2205946
[F:1][CH:2]([F:10])[N:3]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[N:4]1.[Br:11][C:12]1[CH:17]=[C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:15](I)=[CH:14][N:13]=1.C(N(CC)CC)C>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:11][C:12]1[N:13]=[CH:14][C:15]2[CH:9]=[C:8]([C:6]3[CH:5]=[N:4][N:3]([CH:2]([F:10])[F:1])[CH:7]=3)[N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:16]=2[CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 86706267N-(2-Bromo-5-iodopyridin-4-yl)methanesulfonamideHCID 867063321-(difluoromethyl)-4-ethynyl-1H-pyrazole

Produkt 1

HCID 867063336-Bromo-2-(1-(difluoromethyl)-1H-pyrazol-4-yl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridineAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1-(Difluoromethyl)-4-ethynyl-1H-pyrazole (Preparation 152, 187 mg 1.31 mmole) was dissolved in DMF (4.2 mL) and N-(2-bromo-5-iodopyridin-4-yl)methanesulfonamide (Preparation 8, 444 mg 1.17 mmole) was added. To the solution was added triethylamine (0.80 mL, 576 mg 5.7 mmole) and copper(I) iodide (9 mg 0.047 mmole). The reaction was sealed and flushed with nitrogen. Bis(triphenylphosphine)palladium dichloride (37.6 mg 0.046 mmole) was added and the reaction was again flushed with nitrogen, then heated at 60° C. for 140 minutes. The reaction was added to ethyl acetate (45 mL) and washed with water (3×15 mL) and with brine, then dried and concentrated in vacuo. The residue was purified using preparative TLC eluting with 5% ethyl acetate in chloroform to afford the title compound 157 mg. 1H-NMR (d6-acetone, 500 MHz): δ 3.37 (s, 3H), 7.06 (d, J=0.63 Hz, 1H), 7.70 (t, J=59.6 Hz, 1H), 8.04 (s, 1H), 8.16 (m, 1H), 8.51 (s, 1H), 8.73 (d, J=0.95 Hz, 1H).

Aufarbeitung

  1. customThe reaction was sealed
  2. customflushed with nitrogen
  3. customthe reaction was again flushed with nitrogen
  4. additionThe reaction was added to ethyl acetate (45 mL)
  5. washwashed with water (3×15 mL) and with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified
  9. washeluting with 5% ethyl acetate in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-1fb598f8bdb84792a872bcdde4e499ac
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09371319B2

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