Sodium Carbonate → 5-(2-Phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1432325

Reaktionsgleichung

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]#[N:21])=[CH:11]2)(=O)=O)C=CC=CC=1.[O:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.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>[O:22]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=1[C:17]1[CH:18]=[C:13]2[C:12]([C:20]#[N:21])=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

A mixture of 8 (40.0 mg, 0.11 mmol), 2-phenoxyphenylboronic acid (35.5 mg, 0.166 mmol), PdCl2(PPh3)2 (7.8 mg, 0.011 mmol), LiCl (14.0 mg, 0.33 mmol), 1M Na2CO3 (276 μL, 0.28 mmol) in EtOH (0.66 mL) and toluene (0.66 mL) was heated at 105° C. for 0.5 h in a sealed reaction tube. Reaction mixture was separated between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (2×). The combined organic solutions were concentrated and purified by PTLC using ethyl acetate:hexane (1:1) as eluent to give 9 as a white solid (13.8 mg, 40%); 1H NMR (400 MHz, CDCl3) δ 12.80-12.60 (bs, NH), 8.69 (d, J=2.0 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.87 (s, 1H), 7.53 (dd, J=7.6, 1.7 Hz, 1H), 7.40 (dt, J=7.5, 1.8 Hz, 1H), 7.29 (m, 3H), 7.06 (m, 2H), 6.94 (m, 2H); MS (CI) m/z 352.8 (MH+MeCN).

Aufarbeitung

customReaction mixture
customwas separated between ethyl acetate and brine
extractionThe aqueous layer was extracted with ethyl acetate (2×)
concentrationThe combined organic solutions were concentrated
custompurified by PTLC

Quellen und Nachweise

ORD-Eintrag: ord-20bc22df7e4b4a9b81ad04896247c8d1
Quelldatensatz: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07612086B2

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