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Sodium Hydroxide → (2,6-difluorophenyl)-N-[5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)(2-pyridyl)]carboxamide

HRID 874668
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 874668
[CH3:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[Cl-].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1.[CH:28](N(C(C)C)CC)(C)C.[OH-:37].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:28]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([C:3]2[C:2]([CH3:1])=[CH:11][C:6]3[O:7][CH2:8][CH2:9][O:10][C:5]=3[CH:4]=2)=[CH:17][N:16]=1)=[O:37]
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Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 584873735-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)-2-pyridylamineHCID 1317308842,6-Difluorobenzol chloride

Produkt 1

HCID 58487156(2,6-difluorophenyl)-N-[5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)(2-pyridyl)]carboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 183 (30 mg, 0.12 mmol) in CH2Cl2 was added 4-dimethylaminopyridine (DMAP, 1.2 mg, 0.01 mmol), 2,6-difluorobenzol chloride (53 mg, 0.3 mmol) and diisopropylethylamine (DIEA, 62 mg, 0.48 mmol). The reaction mixture was stirred for 2 h at ambient temperature. The reaction was quenched with saturated NaHCO3 (20 ml) and extracted with EtOAc. The organic solvent was removed in vacuo. The residue was dissolved in THF:MeOH (1:1) and added 1N NaOH (2 eq). The mixture was stirred for 10 min at ambient temperature. The reaction solution was concentrated in vacuo and residue was extracted with EtOAc. The crude product was purified by ISCO column and HPLC. Fractions containing pure product were combined and evaporated. The white solid 185 (18.2 mg, 40%) was obtained. LC-MS: calcd. for C21H16F2N2O3: 383 (M+1).

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3 (20 ml)
  2. extractionextracted with EtOAc
  3. customThe organic solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in THF:MeOH (1:1)
  5. stirringThe mixture was stirred for 10 min at ambient temperature
  6. concentrationThe reaction solution was concentrated in vacuo and residue
  7. extractionwas extracted with EtOAc
  8. customThe crude product was purified by ISCO column and HPLC
  9. additionFractions containing pure product
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c493d04bdf79453787cd663bab415146
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08980629B2

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