Sodium Carbonate → HCID 68889701, Verbindung

HRID 2218769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2218769
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=2[CH2:7][O:6][C:5]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:4]1=2.CC1(C)C(C)(C)OB([C:28]2[CH:37]=[CH:36][C:31]3[NH:32][C:33](=[O:35])[NH:34][C:30]=3[CH:29]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:19][C:16]1[CH:17]=[CH:18][C:4]2[C:3](=[CH:2][C:28]3[CH:37]=[CH:36][C:31]4[NH:32][C:33](=[O:35])[NH:34][C:30]=4[CH:29]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=3[CH2:7][O:6][C:5]=2[CH:15]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 67334734HCID 67334734, Verbindung

Produkt 1

HCID 68889701HCID 68889701, VerbindungAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Following procedures essentially as described in Example 219, mix 11-bromomethylene-3,7-difluoro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 68 mg, 0.21 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (52 mg, 0.20 mmol), Na2CO3 (2M in water, 251 μL, 0.503 mmol), dioxane (2 mL), and Pd(PPh3)4 (12 mg, 0.010 mmol). Purify on silica gel (12 g) eluting with THF to afford a brown solid. Triturate with acetone to afford 56 mg (74%) of the title compound as a white solid. HPLC (ISO80-10) t=2.42 min, 96%; MS [ES] 375 (M−H); 1H-NMR (DMSO-d6) δ 10.58 (s, 1H), 10.46 (s, 1H), 7.57 (dd, 1H, J=8.8, 7.0 Hz), 7.24 (m, 2H), 7.00 (s, 1H), 6.81 (m, 2H), 6.72 (m, 2H), 6.64 (dd, 1H, J=10.6, 2.6 Hz), 6.59 (s, 1H), 5.55-5.19 (br d, 2H).

Aufarbeitung

  1. customPurify on silica gel (12 g)
  2. washeluting with THF
  3. customto afford a brown solid
  4. customTriturate with acetone

Quellen und Nachweise

ORD-Eintrag
ord-81247af6293f4d628ee676f4510d76fe
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07411072B2

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