Tri-tert-butylphosphine tetrafluoroborate → Ethyl 3-(3-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)propanoate

HRID 335286

Reaktionsgleichung

Reaktionsgleichung von HRID 335286
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20](=[O:31])[NH:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=4)[CH:17]=[CH:16][C:15]=3[F:32])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[Br-].[CH2:52]([O:54][C:55](=[O:59])[CH2:56][CH2:57][Zn+])[CH3:53]>C1COCC1.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]>[F:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[F:29])[CH2:22][NH:21][C:20]([C:18]1[CH:17]=[CH:16][C:15]([F:32])=[C:14]([NH:13][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([CH2:57][CH2:56][C:55]([O:54][CH2:52][CH3:53])=[O:59])=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:12])[CH:19]=1)=[O:31]

Komponenten

6

Edukt 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 712831817-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide2×HCID 178471816HCID 178471816, Verbindung

Produkt 1

HCID 71283043Ethyl 3-(3-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

7-Bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (Intermediate 3A) (1 g, 1.987 mmol), Pd2(dba)3 (0.091 g, 0.099 mmol) and tritertbutylphosphonium tetrafluoroborate (0.058 g, 0.199 mmol) were combined in THF (60 ml) under nitrogen and the mixture was degassed thoroughly refilling with nitrogen (×3). (3-Ethoxy-3-oxopropyl)zinc(II) bromide (19.87 ml, 9.93 mmol) was added and the mixture was heated at 60° C. for 100 mins. After cooling to RT, the mixture was absorbed onto silica and purification by chromatography eluting with 0-6% MeOH in DCM afforded a yellow oil which was triturated with EtOAc to give the title compound;

Aufarbeitung

  1. customthe mixture was degassed thoroughly
  2. temperatureAfter cooling to RT
  3. customthe mixture was absorbed onto silica and purification by chromatography
  4. washeluting with 0-6% MeOH in DCM
  5. customafforded a yellow oil which
  6. customwas triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-06170f940b2a49999fb86f4774cf1d7d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883819B2

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