Diisopropylethylamine → N-(4-(3-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-2-fluoro-6-methoxybenzamide

HRID 347555

Reaktionsgleichung

Reaktionsgleichung von HRID 347555
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:19])[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.[F:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[C:30]=1[C:31](O)=[O:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:31](=[O:32])[C:30]3[C:34]([O:38][CH3:39])=[CH:35][CH:36]=[CH:37][C:29]=3[F:28])=[CH:14][C:13]=2[F:19])[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 27373602-Fluoro-6-methoxybenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210816594-(3-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine

Produkt 1

HCID 21081788N-(4-(3-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-2-fluoro-6-methoxybenzamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(3-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (400 mg, 0.85 mmol), 2-fluoro-6-methoxybenzoic acid (226 mg, 1.33 mmol), and HATU (641 mg, 1.33 mmol) in DMF (6 mL) was added DIPEA (387 mg, 3 mmol), followed by DMAP (50 mg). The resulting mixture was stirred at rt overnight, diluted with EtOAc, and washed with saturated aq. K2HPO4 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, eluting with 30% EtOAc/CH2Cl2) to give the desired product (370 mg, 72%) as a white solid. LC/MS(ESI+) m/z 605 (M+H)+.

Aufarbeitung

  1. washwashed with saturated aq. K2HPO4 solution and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel, eluting with 30% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-23c97d92fec74328a81ddbc9bb70ff80
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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