Hydrochloric Acid → (spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one-5-yl)boronic acid

HRID 7012

Reaktionsgleichung

Br[CH:2]1[C:6]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].C([Li])CCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C.Cl>C1COCC1>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2([CH:2]([B:27]([OH:28])[OH:26])[CH2:3][CH2:4][CH2:5]2)[C:7]1=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (13.1 g, 53 mmol) in anhydrous THF (300 cm3) under N2, was added sodium hydride (60% in mineral oil, 2.1 g, 53 mmol). After 30 minutes, the reaction mixture was cooled to −78° C. and butyl lithium (2.5 M in hexanes, 22 cm3, 53 mmol) was added slowly. After 30 minutes, tris-iso-propylborate (34 cm3, 146 mmol) was added, and the reaction mixture was slowly brought to room temperature, and stirred for 14 hours. The reaction mixture was poured into 1N HCl and extracted with EtOAc (×3). The organic layers were collected and washed with 1N HCl, water, dried (MgSO4) and evaporated to give the subtitled compound (7.8 g, 64%) as a tan solid which was used without further purification. 1H NMR (DMSO-d6) δ 10.3 (s, 1H), 7.9 (s, 1H), 7.7–7.6 (m, 2H), 6.8 (d, 1H, J=7.7 Hz), 3.4 (s, 1H), 2.0–1.7 (m, 8H); MS (FI-POS) m/z @231.

Aufarbeitung

waitAfter 30 minutes
customwas slowly brought to room temperature
extractionextracted with EtOAc (×3)
customThe organic layers were collected
washwashed with 1N HCl, water
dry with materialdried (MgSO4)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-ed84227053dd4cc8ab8a2904657eb785
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07084168B2

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