Triethylamine → HCID 117771406, Verbindung

HRID 2201526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201526
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[Br:10][C:11]1[N:16]=[C:15]([C:17](O)=[O:18])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl.O>[Br:10][C:11]1[N:16]=[C:15]([C:17]([NH:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:18])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 111923Propylphosphonic anhydrideHCID 714639656-Bromo-3-methoxypicolinic acid

Produkt 1

HCID 117771406HCID 117771406, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3-methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0° C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 8.98 (t, J=6.0 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.39˜7.43 (m, 2H), 7.33 (d, J=8.4 Hz, 2H), 4.22 (d, J=6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355/357.

Aufarbeitung

  1. customFive minutes
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-05e6393fd5374acc85faaf7786881df4
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09364482B2

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