Water → HCID 72203012, Verbindung

HRID 629063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629063
I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1.C([O-])([O-])=O.[Na+].[Na+].O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC.CCO>[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28]([C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[O:6])=[CH:27][N:26]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27367782-Methoxypyrimidine-5-boronic acidHCID 89907516HCID 89907516, Verbindung

Produkt 1

HCID 72203012HCID 72203012, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

3-Iodo-4-methyl-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 13.1, 84 mg, 0.2 mmol), 2-methoxypyrimidin-5-ylboronic acid (61.6 mg, 0.4 mmol), Na2CO3 (63.6 mg, 0.600 mmol), Pd(PPh3)2Cl2 (7.02 mg, 10.00 μmol), water (200 μL), EtOH (133 μL) and DME (1 mL) were added to a vial, which was sealed, evacuated/purged with argon and subjected to MW irradiation at 125° C. for 20 min The RM was diluted with THF (1 mL) and stirred with Si-Thiol (69.4 mg, 0.100 mmol) for a 2 h. The filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 4 g, DCM/MeOH+1% NH4OH, gradient from 1% to 15% MeOH+1% NH4OH) to afford the title compound as a beige solid. UPLC-MS (Condition 1) tR=2.89 min, m/z=404.1 [M+H]+, m/z=402.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.35 (s, 3H) 3.99 (s, 3H) 7.37 (d, J=8.6 Hz, 2H) 7.52 (d, J=8.1 Hz, 1H) 7.88 (d, J=9.3 Hz, 2H), 7.90 (br. s, br. s, 1H) 7.93 (dd, 1H) 8.74 (s, 2H) 10.36 (s, 1H).

Aufarbeitung

  1. customwas sealed
  2. customevacuated/purged with argon
  3. customsubjected to MW irradiation at 125° C. for 20 min The RM
  4. additionwas diluted with THF (1 mL)
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customto give the crude product which
  7. customwas purified by flash chromatography (Silica gel column, 4 g, DCM/MeOH+1% NH4OH, gradient from 1% to 15% MeOH+1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-5a14c00021684c09aa26343f44b7aee5
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315489B2

Notizen zur Reaktion

Wird geladen…