Sodium Carbonate → HCID 59362525, Verbindung

HRID 1625445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625445
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]1[CH:23]=[C:24]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:25][N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=2)=[O:33])[C:27]1=[O:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12]([C:40]3[CH:41]=[C:36]([CH:37]=[CH:38][CH:39]=3)[CH2:35][NH:34][C:32]([C:28]3[C:27](=[O:45])[N:26]([CH2:25][C:24]4[CH:46]=[CH:47][C:48]([F:49])=[C:22]([F:21])[CH:23]=4)[CH:31]=[CH:30][CH:29]=3)=[O:33])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridineHCID 59362353HCID 59362353, Verbindung

Produkt 1

HCID 59362525HCID 59362525, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Into a vial was dissolved 1-benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (581 mg, 0.00125 mol) and 3-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenylboronic acid (453 mg, 0.00114 mol) and palladium acetate (13 mg, 0.000057 mol; Strem) and triphenylphosphine (32 mg, 0.00012 mol; Aldrich) in acetone (5.4 mL, Acros;). To this was added 2.0 M of sodium carbonate in water (1.8 mL). The vial was flushed under an atmosphere of argon and sealed and was heated at 75 Celsius for 1 hour. The reaction was evaporated then diluted with methylene chloride, washed with water, dried with magnesium sulfate, filtered, and concentrated. The residue was taken up in methylene chloride and purified by silica gel chromatography using hexanes/ethyl acetate as eluent (Rf=0.33 in 1:3 hexanes/ethyl acetate) to yield 663.8 mg (85%) of product. MS m/z=689.09 M+H.

Aufarbeitung

  1. customThe vial was flushed under an atmosphere of argon
  2. customsealed
  3. customThe reaction was evaporated
  4. additionthen diluted with methylene chloride
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f9206798bf2f4424b2a7930a856aa84b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778977B2

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